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An acid is a
molecule A molecule is an electrically Electricity is the set of physical phenomena associated with the presence and motion Image:Leaving Yongsan Station.jpg, 300px, Motion involves a change in position In physics, motion is the phenomenon ...

molecule
or
ion An ion () is an atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday objects that can be touched are ...
capable of donating a
proton A proton is a subatomic particle, symbol or , with a positive electric charge of +1''e'' elementary charge and a mass slightly less than that of a neutron. Protons and neutrons, each with masses of approximately one atomic mass unit, are collecti ...

proton
(hydrogen ion H+) (a Brønsted–Lowry acid), or, alternatively, capable of forming a
covalent bond A covalent bond is a chemical bond that involves the sharing of electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs, and the stable balance of attractive and repulsive forces between atoms, when they s ...
with an
electron pair In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they underg ...
(a
Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty Non-bonding orbital, orbital which is capable of accepting an electron pair from a Lewis Base (chemistry), base to form a Lewis ad ...

Lewis acid
).IUPAC Gold Book - acid
/ref> The first category of acids are the proton donors, or Brønsted–Lowry acids. In the special case of
aqueous solutions An aqueous solution is a solution Image:SaltInWaterSolutionLiquid.jpg, Making a saline water solution by dissolving Salt, table salt (sodium chloride, NaCl) in water. The salt is the solute and the water the solvent. In chemistry, a solution ...
, proton donors form the
hydronium ion In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an occurrence in th ...
H3O+ and are known as Arrhenius acids. Brønsted and
LowryLowry may refer to: People Lowry is a common surname, and may refer to: * Calvin Lowry (born 1983), American football player * Dave Lowry (born 1965), Canadian ice hockey player * Desiree Lowry (born 1972), Puerto Rican beauty pageant titleholder ...

Lowry
generalized the Arrhenius theory to include non-aqueous solvents. A Brønsted or Arrhenius acid usually contains a hydrogen atom bonded to a chemical structure that is still energetically favorable after loss of H+. Aqueous Arrhenius acids have characteristic properties which provide a practical description of an acid. Acids form
aqueous solution An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a saline water solution by dissolving Salt, table salt (sodium chloride, NaCl) in water. The salt is the solute an ...
s with a sour taste, can turn blue
litmus Litmus is a water-soluble In chemistry, solubility is ability of a chemical substance, substance, the solute, to form a solution (chemistry), solution with another substance, the solvent. Insolubility is the opposite property, the inabili ...
red, and react with bases and certain metals (like
calcium Calcium is a chemical element In chemistry, an element is a pure Chemical substance, substance consisting only of atoms that all have the same numbers of protons in their atomic nucleus, nuclei. Unlike chemical compounds, chemical elem ...

calcium
) to form
salts In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during ...
. The word ''acid'' is derived from the
Latin Latin (, or , ) is a classical language belonging to the Italic languages, Italic branch of the Indo-European languages. Latin was originally spoken in the area around Rome, known as Latium. Through the power of the Roman Republic, it became ...

Latin
''acidus/acēre'', meaning 'sour'. An aqueous solution of an acid has a less than 7 and is colloquially also referred to as "acid" (as in "dissolved in acid"), while the strict definition refers only to the
solute In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an occurrence i ...
. A lower pH means a higher acidity, and thus a higher concentration of positive hydrogen ions in the
solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a saline water solution by dissolving Salt, table salt (sodium chloride, NaCl) in water. The salt is the solute and the water the solvent. In chemistry ...
. Chemicals or substances having the property of an acid are said to be acidic. Common aqueous acids include
hydrochloric acid Hydrochloric acid +(aq) Cl−(aq) or H3O+ Cl− also known as muriatic acid, is an aqueous solution An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a salin ...

hydrochloric acid
(a solution of
hydrogen chloride The compound Compound may refer to: Architecture and built environments * Compound (enclosure), a cluster of buildings having a shared purpose, usually inside a fence or wall ** Compound (fortification), a version of the above fortified with ...

hydrogen chloride
which is found in
gastric acid Gastric acid, gastric juice, or stomach acid, is a digestive fluid formed within the stomach lining. With a pH between 1 and 3, gastric acid An acid is a or capable of donating a (hydrogen ion H+) (a ), or, alternatively, capable of for ...
in the stomach and activates
digestive enzymes Digestive enzymes are a group of enzyme Enzymes () are proteins that act as biological catalysts (biocatalysts). Catalysts accelerate chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, a ...
),
acetic acid Acetic acid , systematically named ethanoic acid , is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is no less than 4% acetic acid by volume, making acetic acid ...

acetic acid
(vinegar is a dilute aqueous solution of this liquid),
sulfuric acid Sulfuric acid (American spelling Despite the various English dialects spoken from country to country and within different regions of the same country, there are only slight regional variations in English orthography English orthogra ...

sulfuric acid
(used in
car batteries An automotive battery or car battery is a rechargeable battery that is used to start a motor vehicle. Its main purpose is to provide an electric current to the electric-powered starting motor, which in turn starts the chemically-powered internal ...
), and
citric acid Citric acid is an organic compound In , organic compounds are generally any s that contain - . Due to carbon's ability to (form chains with other carbon s), millions of organic compounds are known. The study of the properties, reactions, ...

citric acid
(found in citrus fruits). As these examples show, acids (in the colloquial sense) can be solutions or pure substances, and can be derived from acids (in the strict sense) that are solids, liquids, or gases.
Strong acid Acid strength is the tendency of an acid An acid is a or capable of donating a (hydrogen ion H+) (a ), or, alternatively, capable of forming a with an (a ). The first category of acids are the proton donors, or s. In the special ca ...

Strong acid
s and some concentrated weak acids are corrosive, but there are exceptions such as
carborane Carboranes are electron-delocalized (non-classically bonded) clusters composed of , and atoms that may also contain other metallic and nonmetallic elements in the cluster framework.Grimes, R. N., ''Carboranes 3rd Ed.'', Elsevier, Amsterdam and N ...
s and
boric acid Boric acid, also called hydrogen borate, boracic acid, and orthoboric acid is a weak, monobasic Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is ...

boric acid
. The second category of acids are
Lewis acids A Lewis acid is a chemical species that contains an empty orbital which is capable of accepting an electron pair In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds c ...
, which form a covalent bond with an electron pair. An example is
boron trifluoride Boron trifluoride is the inorganic compound with the chemical formula, formula BF3. This pungent colourless toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds. Structure ...
(BF3), whose boron atom has a vacant orbital which can form a covalent bond by sharing a lone pair of electrons on an atom in a base, for example the nitrogen atom in
ammonia Ammonia is a chemical compound, compound of nitrogen and hydrogen with the chemical formula, formula NH3. A Binary compounds of hydrogen, stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct ch ...

ammonia
(NH3).
Lewis Lewis may refer to: Names * Lewis (given name) Lewis () is a masculine English given name, English-language given name. It was coined as an anglicisation of given names in other languages. "Lewis" has been used to anglicise the Irish language, Ir ...
considered this as a generalization of the Brønsted definition, so that an acid is a chemical species that accepts electron pairs either directly ''or'' by releasing protons (H+) into the solution, which then accept electron pairs. However, hydrogen chloride, acetic acid, and most other Brønsted–Lowry acids cannot form a covalent bond with an electron pair and are therefore not Lewis acids. Conversely, many Lewis acids are not Arrhenius or Brønsted–Lowry acids. In modern terminology, an ''acid'' is implicitly a Brønsted acid and not a Lewis acid, since chemists almost always refer to a Lewis acid explicitly as ''a Lewis acid''.


Definitions and concepts

Modern definitions are concerned with the fundamental chemical reactions common to all acids. Most acids encountered in everyday life are
aqueous solutions An aqueous solution is a solution Image:SaltInWaterSolutionLiquid.jpg, Making a saline water solution by dissolving Salt, table salt (sodium chloride, NaCl) in water. The salt is the solute and the water the solvent. In chemistry, a solution ...
, or can be dissolved in water, so the Arrhenius and Brønsted–Lowry definitions are the most relevant. The Brønsted–Lowry definition is the most widely used definition; unless otherwise specified, acid–base reactions are assumed to involve the transfer of a proton (H+) from an acid to a base. Hydronium ions are acids according to all three definitions. Although alcohols and amines can be Brønsted–Lowry acids, they can also function as
Lewis base A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty Non-bonding orbital, orbital which is capable of accepting an electron pair from a Lewis Base (chemistry), base to form a Lewis ad ...
s due to the lone pairs of electrons on their oxygen and nitrogen atoms.


Arrhenius acids

In 1884,
Svante Arrhenius Svante August Arrhenius ( , ; 19 February 1859 – 2 October 1927) was a . Originally a , but often referred to as a , Arrhenius was one of the founders of the science of . He received the in 1903, becoming the first Nobel laureate. In 1905, ...

Svante Arrhenius
attributed the properties of acidity to
hydrogen ion A hydrogen ion is created when a hydrogen Hydrogen is the chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the chemical elements In chemistry, an element is a pure substance cons ...
s (H+), later described as
protons A proton is a subatomic particle, symbol or , with a positive electric charge Electric charge is the physical property of matter that causes it to experience a force when placed in an electromagnetic field. There are two types of electric cha ...
or hydrons. An Arrhenius acid is a substance that, when added to water, increases the concentration of H+ ions in the water. Note that chemists often write H+(''aq'') and refer to the
hydrogen ion A hydrogen ion is created when a hydrogen Hydrogen is the chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the chemical elements In chemistry, an element is a pure substance cons ...
when describing acid–base reactions but the free hydrogen nucleus, a
proton A proton is a subatomic particle, symbol or , with a positive electric charge of +1''e'' elementary charge and a mass slightly less than that of a neutron. Protons and neutrons, each with masses of approximately one atomic mass unit, are collecti ...

proton
, does not exist alone in water, it exists as the hydronium ion (H3O+) or other forms (H5O2+, H9O4+). Thus, an Arrhenius acid can also be described as a substance that increases the concentration of hydronium ions when added to water. Examples include molecular substances such as hydrogen chloride and acetic acid. An Arrhenius
base Base or BASE may refer to: Brands and enterprises * Base (mobile telephony provider), a Belgian mobile telecommunications operator *Base CRM Base CRM (originally Future Simple or PipeJump) is an enterprise software company based in Mountain Vie ...
, on the other hand, is a substance which increases the concentration of
hydroxide Hydroxide is a diatomic anion with chemical formula A chemical formula is a way of presenting information about the chemical proportions of s that constitute a particular or molecule, using symbols, numbers, and sometimes also other sym ...
(OH) ions when dissolved in water. This decreases the concentration of hydronium because the ions react to form H2O molecules: H3O + OH ⇌ H2O(l) + H2O(l) Due to this equilibrium, any increase in the concentration of hydronium is accompanied by a decrease in the concentration of hydroxide. Thus, an Arrhenius acid could also be said to be one that decreases hydroxide concentration, while an Arrhenius base increases it. In an acidic solution, the concentration of hydronium ions is greater than 10−7 moles per liter. Since pH is defined as the negative logarithm of the concentration of hydronium ions, acidic solutions thus have a pH of less than 7.


Brønsted–Lowry acids

While the Arrhenius concept is useful for describing many reactions, it is also quite limited in its scope. In 1923 chemists Johannes Nicolaus Brønsted and
Thomas Martin Lowry Thomas Martin Lowry (; 26 October 1874 – 2 November 1936) was an English English usually refers to: * English language English is a West Germanic languages, West Germanic language first spoken in History of Anglo-Saxon England, early ...

Thomas Martin Lowry
independently recognized that acid–base reactions involve the transfer of a proton. A Brønsted–Lowry acid (or simply Brønsted acid) is a species that donates a proton to a Brønsted–Lowry base. Brønsted–Lowry acid–base theory has several advantages over Arrhenius theory. Consider the following reactions of
acetic acid Acetic acid , systematically named ethanoic acid , is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is no less than 4% acetic acid by volume, making acetic acid ...

acetic acid
(CH3COOH), the
organic acid An organic acid is an organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, beha ...
that gives vinegar its characteristic taste: : + + : + + Both theories easily describe the first reaction: CH3COOH acts as an Arrhenius acid because it acts as a source of H3O+ when dissolved in water, and it acts as a Brønsted acid by donating a proton to water. In the second example CH3COOH undergoes the same transformation, in this case donating a proton to ammonia (NH3), but does not relate to the Arrhenius definition of an acid because the reaction does not produce hydronium. Nevertheless, CH3COOH is both an Arrhenius and a Brønsted–Lowry acid. Brønsted–Lowry theory can be used to describe reactions of in nonaqueous solution or the gas phase.
Hydrogen chloride The compound Compound may refer to: Architecture and built environments * Compound (enclosure), a cluster of buildings having a shared purpose, usually inside a fence or wall ** Compound (fortification), a version of the above fortified with ...

Hydrogen chloride
(HCl) and ammonia combine under several different conditions to form
ammonium chloride Ammonium chloride is an inorganic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, ...

ammonium chloride
, NH4Cl. In aqueous solution HCl behaves as
hydrochloric acid Hydrochloric acid +(aq) Cl−(aq) or H3O+ Cl− also known as muriatic acid, is an aqueous solution An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a salin ...

hydrochloric acid
and exists as hydronium and chloride ions. The following reactions illustrate the limitations of Arrhenius's definition: # H3O + Cl + NH3 → Cl + NH(aq) + H2O # HCl(benzene) + NH3(benzene) → NH4Cl(s) # HCl(g) + NH3(g) → NH4Cl(s) As with the acetic acid reactions, both definitions work for the first example, where water is the solvent and hydronium ion is formed by the HCl solute. The next two reactions do not involve the formation of ions but are still proton-transfer reactions. In the second reaction hydrogen chloride and ammonia (dissolved in
benzene Benzene is an organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ (anatomy), organ Chemistry * Organic matter, matter that has come from a once-living organ ...

benzene
) react to form solid ammonium chloride in a benzene solvent and in the third gaseous HCl and NH3 combine to form the solid.


Lewis acids

A third, only marginally related concept was proposed in 1923 by Gilbert N. Lewis, which includes reactions with acid–base characteristics that do not involve a proton transfer. A Lewis acid is a species that accepts a pair of electrons from another species; in other words, it is an electron pair acceptor. Brønsted acid–base reactions are proton transfer reactions while Lewis acid–base reactions are electron pair transfers. Many Lewis acids are not Brønsted–Lowry acids. Contrast how the following reactions are described in terms of acid–base chemistry: : In the first reaction a fluoride ion, F, gives up an
electron pair In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they underg ...
to
boron trifluoride Boron trifluoride is the inorganic compound with the chemical formula, formula BF3. This pungent colourless toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds. Structure ...
to form the product
tetrafluoroborate Tetrafluoroborate is the anion An ion () is a particle, atom or molecule with a net electric charge, electrical charge. The charge of the electron is considered negative by convention. The negative charge of an ion is equal and opposite to ...

tetrafluoroborate
. Fluoride "loses" a pair of
valence electron In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during ...
s because the electrons shared in the B—F bond are located in the region of space between the two atomic
nuclei ''Nucleus'' (plural nuclei) is a Latin word for the seed inside a fruit. It most often refers to: *Atomic nucleus, the very dense central region of an atom *Cell nucleus, a central organelle of a eukaryotic cell, containing most of the cell's DNA ...
and are therefore more distant from the fluoride nucleus than they are in the lone fluoride ion. BF3 is a Lewis acid because it accepts the electron pair from fluoride. This reaction cannot be described in terms of Brønsted theory because there is no proton transfer. The second reaction can be described using either theory. A proton is transferred from an unspecified Brønsted acid to ammonia, a Brønsted base; alternatively, ammonia acts as a Lewis base and transfers a lone pair of electrons to form a bond with a hydrogen ion. The species that gains the electron pair is the Lewis acid; for example, the oxygen atom in H3O+ gains a pair of electrons when one of the H—O bonds is broken and the electrons shared in the bond become localized on oxygen. Depending on the context, a Lewis acid may also be described as an
oxidizer An oxidizing agent, also known as an oxidant or oxidizer, is a substance that has the ability to oxidize other substances — in other words to electron acceptor, accept their electrons. Common oxidizing agents are oxygen, hydrogen peroxi ...

oxidizer
or an
electrophile In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during a ...
. Organic Brønsted acids, such as acetic, citric, or oxalic acid, are not Lewis acids. They dissociate in water to produce a Lewis acid, H+, but at the same time also yield an equal amount of a Lewis base (acetate, citrate, or oxalate, respectively, for the acids mentioned). This article deals mostly with Brønsted acids rather than Lewis acids.


Dissociation and equilibrium

Reactions of acids are often generalized in the form HA H+ + A, where HA represents the acid and A is the
conjugate base A conjugate acid, within the Brønsted–Lowry acid–base theory The Brønsted–Lowry theory (also called proton theory of acids and bases) is an acid–base reaction theory which was proposed independently by Johannes Nicolaus Brønsted ...
. This reaction is referred to as protolysis. The protonated form (HA) of an acid is also sometimes referred to as the free acid. Acid–base conjugate pairs differ by one proton, and can be interconverted by the addition or removal of a proton (
protonation In chemistry, protonation (or hydronation) is the addition of a proton (or hydron, or hydrogen cation), (H+) to an atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance ...
and
deprotonation Deprotonation (or dehydronation) is the removal (transfer) of a proton A proton is a subatomic particle, symbol or , with a positive electric charge of +1''e'' elementary charge and a mass slightly less than that of a neutron. Protons and neutr ...

deprotonation
, respectively). Note that the acid can be the charged species and the conjugate base can be neutral in which case the generalized reaction scheme could be written as HA+ H+ + A. In solution there exists an
equilibrium List of types of equilibrium, the condition of a system in which all competing influences are balanced, in a wide variety of contexts. Equilibrium may also refer to: Film and television * Equilibrium (film), ''Equilibrium'' (film), a 2002 scien ...
between the acid and its conjugate base. The
equilibrium constant The equilibrium constant of a chemical reaction is the value of its reaction quotient at chemical equilibrium, a state approached by a dynamic chemical system after sufficient time has elapsed at which its composition has no measurable tendency ...
''K'' is an expression of the equilibrium concentrations of the molecules or the ions in solution. Brackets indicate concentration, such that 2Omeans ''the concentration of H2O''. The
acid dissociation constant An acid dissociation constant, ''K''a, (also known as acidity constant, or acid-ionization constant) is a quantitative measure of the strength Physical strength *Physical strength, as in people or animals *Hysterical strength, extreme str ...
''K''a is generally used in the context of acid–base reactions. The numerical value of ''K''a is equal to the product of the concentrations of the products divided by the concentration of the reactants, where the reactant is the acid (HA) and the products are the conjugate base and H+. :K_a = \frac\ce\ce The stronger of two acids will have a higher ''K''a than the weaker acid; the ratio of hydrogen ions to acid will be higher for the stronger acid as the stronger acid has a greater tendency to lose its proton. Because the range of possible values for ''K''a spans many orders of magnitude, a more manageable constant, p''K''a is more frequently used, where p''K''a = −log10 ''K''a. Stronger acids have a smaller p''K''a than weaker acids. Experimentally determined p''K''a at 25 °C in aqueous solution are often quoted in textbooks and reference material.


Nomenclature

Arrhenius acids are named according to their
anion An ion () is an atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday objects that can be touched are ...
s. In the classical naming system, the ionic suffix is dropped and replaced with a new suffix, according to the table following. The prefix "hydro-" is used when the acid is made up of just hydrogen and one other element. For example, HCl has
chloride The chloride ion An ion () is an atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday objects th ...

chloride
as its anion, so the hydro- prefix is used, and the -ide suffix makes the name take the form
hydrochloric acid Hydrochloric acid +(aq) Cl−(aq) or H3O+ Cl− also known as muriatic acid, is an aqueous solution An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a salin ...

hydrochloric acid
. ''Classical naming system:'' In the
IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering OrganizationsNational Adhering Organizations in chemistry are the organizations that work as the authoritative power over chemist ...
naming system, "aqueous" is simply added to the name of the ionic compound. Thus, for hydrogen chloride, as an acid solution, the IUPAC name is aqueous hydrogen chloride.


Acid strength

The strength of an acid refers to its ability or tendency to lose a proton. A strong acid is one that completely dissociates in water; in other words, one
mole Mole (or Molé) may refer to: Animals * Mole (animal) or "true mole", mammals in the family Talpidae, found in Eurasia and North America * Golden moles, southern African mammals in the family Chrysochloridae, similar to but unrelated to Talpidae ...
of a strong acid HA dissolves in water yielding one mole of H+ and one mole of the conjugate base, A, and none of the protonated acid HA. In contrast, a weak acid only partially dissociates and at equilibrium both the acid and the conjugate base are in solution. Examples of
strong acid Acid strength is the tendency of an acid An acid is a or capable of donating a (hydrogen ion H+) (a ), or, alternatively, capable of forming a with an (a ). The first category of acids are the proton donors, or s. In the special ca ...

strong acid
s are
hydrochloric acid Hydrochloric acid +(aq) Cl−(aq) or H3O+ Cl− also known as muriatic acid, is an aqueous solution An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a salin ...

hydrochloric acid
(HCl),
hydroiodic acid Hydroiodic acid (or hydriodic acid) is an aqueous solution An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a saline water solution by dissolving Salt, table sa ...
(HI),
hydrobromic acid Hydrobromic acid is a strong acid Acid strength is the tendency of an acid An acid is a or capable of donating a (hydrogen ion H+) (a ), or, alternatively, capable of forming a with an (a ). The first category of acids are the pr ...

hydrobromic acid
(HBr),
perchloric acid Perchloric acid is a mineral acid A mineral acid (or inorganic acid) is an acid An acid is a molecule or ion An ion () is a particle In the Outline of physical science, physical sciences, a particle (or corpuscule in older texts) ...
(HClO4),
nitric acid Nitric acid (), also known as ''aqua fortis'' (Latin for "strong water") and spirit of niter, is a highly corrosive mineral acid. The pure compound is colorless, but older samples tend to acquire a yellow cast due to decomposition into nitroge ...

nitric acid
(HNO3) and
sulfuric acid Sulfuric acid (American spelling Despite the various English dialects spoken from country to country and within different regions of the same country, there are only slight regional variations in English orthography English orthogra ...

sulfuric acid
(H2SO4). In water each of these essentially ionizes 100%. The stronger an acid is, the more easily it loses a proton, H+. Two key factors that contribute to the ease of deprotonation are the
polarity Polarity may refer to: Science *Polarity (mutual inductance), the relationship between components such as transformer windings *Polarity (projective geometry), in mathematics, a duality of order two *Polarity in embryogenesis, the animal and vegeta ...
of the H—A bond and the size of atom A, which determines the strength of the H—A bond. Acid strengths are also often discussed in terms of the stability of the conjugate base. Stronger acids have a larger
acid dissociation constant An acid dissociation constant, ''K''a, (also known as acidity constant, or acid-ionization constant) is a quantitative measure of the strength Physical strength *Physical strength, as in people or animals *Hysterical strength, extreme str ...
, ''K''a and a more negative p''K''a than weaker acids. Sulfonic acids, which are organic oxyacids, are a class of strong acids. A common example is
toluenesulfonic acid ''p''-Toluenesulfonic acid (PTSA or ''p''TsOH) or tosylic acid (TsOH) is an organic compound with the formula methyl group, CH3benzene, C6H4Sulfonic acid, SO3H. It is a white extremely hygroscopic solid that is soluble in water, Alcohol (chemistr ...
(tosylic acid). Unlike sulfuric acid itself, sulfonic acids can be solids. In fact,
polystyrene Polystyrene (PS) is a synthetic Aromaticity, aromatic hydrocarbon polymer made from the monomer known as styrene. Polystyrene can be solid or foamed. General-purpose polystyrene is clear, hard, and brittle. It is an inexpensive resin per un ...

polystyrene
functionalized into polystyrene sulfonate is a solid strongly acidic plastic that is filterable.
Superacid According to the classical definition, a superacid is an acid An acid is a or capable of donating a (hydrogen ion H+) (a ), or, alternatively, capable of forming a with an (a ). The first category of acids are the proton donors, or s. ...
s are acids stronger than 100% sulfuric acid. Examples of superacids are
fluoroantimonic acid Fluoroantimonic acid is a mixture of hydrogen fluoride and antimony pentafluoride, containing various cations and anions (the simplest being and ). This substance is a superacid, that can be over a billion times stronger than 100% pure sulfuric ...

fluoroantimonic acid
,
magic acid Magic acid (FSO3H·SbF5) is a superacid consisting of a mixture, most commonly in a 1:1 molar ratio, of fluorosulfuric acid Fluorosulfuric acid (IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federat ...
and
perchloric acid Perchloric acid is a mineral acid A mineral acid (or inorganic acid) is an acid An acid is a molecule or ion An ion () is a particle In the Outline of physical science, physical sciences, a particle (or corpuscule in older texts) ...
. Superacids can permanently protonate water to give ionic, crystalline
hydronium In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an occurrence in th ...

hydronium
"salts". They can also quantitatively stabilize
carbocation A carbocation () is an ion An ion () is an atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday ...
s. While ''K''a measures the strength of an acid compound, the strength of an aqueous acid solution is measured by pH, which is an indication of the concentration of hydronium in the solution. The pH of a simple solution of an acid compound in water is determined by the dilution of the compound and the compound's ''K''a.


Lewis acid strength in non-aqueous solutions

Lewis acids A Lewis acid is a chemical species that contains an empty orbital which is capable of accepting an electron pair In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds c ...
have been classified in the
ECW model In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an occurrence in the ...
and it has been shown that there is no one order of acid strengths. The relative acceptor strength of Lewis acids toward a series of bases, versus other Lewis acids, can be illustrated by C-B plots. It has been shown that to define the order of Lewis acid strength at least two properties must be considered. For Pearson's qualitative
HSAB theory HSAB concept is an initialism An acronym is a word In linguistics, a word of a spoken language can be defined as the smallest sequence of phonemes that can be uttered in isolation with semantic, objective or pragmatics, practical meaning (lin ...
the two properties are
hardness Hardness (antonym: softness) is a measure of the resistance to localized plastic deformation In engineering, deformation refers to the change in size or shape of an object. ''Displacements'' are the ''absolute'' change in position of a point ...
and strength while for Drago’s quantitative ECW model the two properties are electrostatic and covalent.


Chemical characteristics


Monoprotic acids

Monoprotic acids, also known as monobasic acids, are those acids that are able to donate one
proton A proton is a subatomic particle, symbol or , with a positive electric charge of +1''e'' elementary charge and a mass slightly less than that of a neutron. Protons and neutrons, each with masses of approximately one atomic mass unit, are collecti ...

proton
per molecule during the process of dissociation (sometimes called ionization) as shown below (symbolized by HA): :HA(aq) + H2O(l) H3O + A         ''K''a Common examples of monoprotic acids in
mineral acid A mineral acid (or inorganic acid) is an acid An acid is a or capable of donating a (hydrogen ion H+) (a ), or, alternatively, capable of forming a with an (a ). The first category of acids are the proton donors, or s. In the special ...
s include
hydrochloric acid Hydrochloric acid +(aq) Cl−(aq) or H3O+ Cl− also known as muriatic acid, is an aqueous solution An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a salin ...

hydrochloric acid
(HCl) and
nitric acid Nitric acid (), also known as ''aqua fortis'' (Latin for "strong water") and spirit of niter, is a highly corrosive mineral acid. The pure compound is colorless, but older samples tend to acquire a yellow cast due to decomposition into nitroge ...

nitric acid
(HNO3). On the other hand, for
organic acids An organic acid is an organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to Catenation, ...
the term mainly indicates the presence of one
carboxylic acid A carboxylic acid is an organic acid that contains a carboxyl group (C(=O)OH) attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with substituent, R referring to the alkyl, alkenyl, aryl, or other group. ...
group and sometimes these acids are known as monocarboxylic acid. Examples in
organic acids An organic acid is an organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to Catenation, ...
include
formic acid Formic acid, systematically named methanoic acid, is the simplest carboxylic acid A carboxylic acid is an organic acid An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acid ...

formic acid
(HCOOH),
acetic acid Acetic acid , systematically named ethanoic acid , is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is no less than 4% acetic acid by volume, making acetic acid ...

acetic acid
(CH3COOH) and
benzoic acid Benzoic acid is a white (or colorless) solid with the formula C6H5CO2H. It is the simplest aromatic forms of benzene (top) combine to produce an average structure (bottom) In chemistry, aromaticity is a property of cyclic compound, cyclic ( ...

benzoic acid
(C6H5COOH).


Polyprotic acids

Polyprotic acids, also known as polybasic acids, are able to donate more than one proton per acid molecule, in contrast to monoprotic acids that only donate one proton per molecule. Specific types of polyprotic acids have more specific names, such as diprotic (or dibasic) acid (two potential protons to donate), and triprotic (or tribasic) acid (three potential protons to donate). A diprotic acid (here symbolized by H2A) can undergo one or two dissociations depending on the pH. Each dissociation has its own dissociation constant, Ka1 and Ka2. : : The first dissociation constant is typically greater than the second; i.e., ''K''a1 > ''K''a2. For example,
sulfuric acid Sulfuric acid (American spelling Despite the various English dialects spoken from country to country and within different regions of the same country, there are only slight regional variations in English orthography English orthogra ...

sulfuric acid
(H2SO4) can donate one proton to form the
bisulfate The sulfate or sulphate ion is a polyatomic anion An ion () is a particle, atom or molecule with a net electric charge, electrical charge. The charge of the electron is considered negative by convention. The negative charge of an ion is ...
anion (HSO), for which ''K''a1 is very large; then it can donate a second proton to form the
sulfate The sulfate or sulphate ion is a polyatomic anion An ion () is an atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having ...

sulfate
anion (SO), wherein the ''K''a2 is intermediate strength. The large ''K''a1 for the first dissociation makes sulfuric a strong acid. In a similar manner, the weak unstable
carbonic acid In chemistry, carbonic acid is a dibasic acid with the chemical formula A chemical formula is a way of presenting information about the chemical proportions of s that constitute a particular or molecule, using symbols, numbers, and s ...

carbonic acid
can lose one proton to form
bicarbonate In inorganic chemistry, bicarbonate (International Union of Pure and Applied Chemistry, IUPAC-recommended nomenclature: hydrogen carbonate) is an intermediate form in the deprotonation of carbonic acid. It is a Polyatomic ion, polyatomic anion w ...

bicarbonate
anion and lose a second to form
carbonate In chemistry, a carbonate is a salt Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of Salt (chemistry), salts; salt in its natural form as a crystallinity, crystalline mi ...

carbonate
anion (CO). Both ''K''a values are small, but ''K''a1 > ''K''a2 . A triprotic acid (H3A) can undergo one, two, or three dissociations and has three dissociation constants, where ''K''a1 > ''K''a2 > ''K''a3. : : : An
inorganic In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they under ...
example of a triprotic acid is orthophosphoric acid (H3PO4), usually just called
phosphoric acid Phosphoric acid, also known as orthophosphoric acid or phosphoric(V) acid, is a weak acid with the chemical formula . The pure compound is a colorless solid. All three hydrogens are acidic to varying degrees and can be lost from the molecule ...

phosphoric acid
. All three protons can be successively lost to yield H2PO, then HPO, and finally PO, the orthophosphate ion, usually just called
phosphate In chemistry, a phosphate is an anion, salt (chemistry), salt, functional group or ester derived from a phosphoric acids and phosphates, phosphoric acid. It most commonly means orthophosphate, a derivative of phosphoric acid, orthophosphoric a ...

phosphate
. Even though the positions of the three protons on the original phosphoric acid molecule are equivalent, the successive ''K''a values differ since it is energetically less favorable to lose a proton if the conjugate base is more negatively charged. An
organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ (anatomy), organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or ...
example of a triprotic acid is
citric acid Citric acid is an organic compound In , organic compounds are generally any s that contain - . Due to carbon's ability to (form chains with other carbon s), millions of organic compounds are known. The study of the properties, reactions, ...

citric acid
, which can successively lose three protons to finally form the
citrate Citric acid is an organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behav ...
ion. Although the subsequent loss of each hydrogen ion is less favorable, all of the conjugate bases are present in solution. The fractional concentration, ''α'' (alpha), for each species can be calculated. For example, a generic diprotic acid will generate 3 species in solution: H2A, HA, and A2−. The fractional concentrations can be calculated as below when given either the pH (which can be converted to the + or the concentrations of the acid with all its conjugate bases: :\begin \alpha_\ce &= \frac = \frac\\ \alpha_\ce &= \frac = \frac\\ \alpha_\ce&= \frac = \frac \end A plot of these fractional concentrations against pH, for given ''K''1 and ''K''2, is known as a
Bjerrum plotBjerrum may refer to: ;People * Niels Janniksen Bjerrum (1879 – 1958), was a Danish chemist (son of Jannik Petersen Bjerrum and father of Jannik Bjerrum). * Jannik Bjerrum (1909 – 1992), was a Danish chemist (son of Niels Janniksen Bjerrum). * ...
. A pattern is observed in the above equations and can be expanded to the general ''n'' -protic acid that has been deprotonated ''i'' -times: : \alpha_= where ''K''0 = 1 and the other K-terms are the dissociation constants for the acid.


Neutralization

Neutralization is the reaction between an acid and a base, producing a
salt Salt is a mineral In geology and mineralogy, a mineral or mineral species is, broadly speaking, a solid chemical compound with a fairly well-defined chemical composition and a specific crystal structure that occurs naturally in pure fo ...
and neutralized base; for example,
hydrochloric acid Hydrochloric acid +(aq) Cl−(aq) or H3O+ Cl− also known as muriatic acid, is an aqueous solution An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a salin ...

hydrochloric acid
and
sodium hydroxide Sodium hydroxide, also known as lye A lye is a metal hydroxide traditionally obtained by leaching wood ashes, or a strong alkali In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chem ...

sodium hydroxide
form
sodium chloride Sodium chloride , commonly known as salt (although sea salt also contains other chemical salt (chemistry), salts), is an ionic compound with the chemical formula NaCl, representing a 1:1 ratio of sodium and chloride ions. With Molar mass, molar ...
and water: :HCl(aq) + NaOH(aq) → H2O(l) + NaCl(aq) Neutralization is the basis of
titration Titration (also known as titrimetry and volumetric analysis) is a common laboratory method of quantitative chemical analysis Analytical chemistry studies and uses instruments and methods used to separate, identify, and quantify matter. In pr ...

titration
, where a
pH indicator A pH indicator is a halochromism, halochromic chemical compound added in small amounts to a Solution (chemistry), solution so the pH (acidity or Base (chemistry), basicity) of the solution can be determined visually. Hence, a pH indicator is a ...
shows equivalence point when the equivalent number of moles of a base have been added to an acid. It is often wrongly assumed that neutralization should result in a solution with pH 7.0, which is only the case with similar acid and base strengths during a reaction. Neutralization with a base weaker than the acid results in a weakly acidic salt. An example is the weakly acidic
ammonium chloride Ammonium chloride is an inorganic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, ...

ammonium chloride
, which is produced from the strong acid
hydrogen chloride The compound Compound may refer to: Architecture and built environments * Compound (enclosure), a cluster of buildings having a shared purpose, usually inside a fence or wall ** Compound (fortification), a version of the above fortified with ...

hydrogen chloride
and the weak base
ammonia Ammonia is a chemical compound, compound of nitrogen and hydrogen with the chemical formula, formula NH3. A Binary compounds of hydrogen, stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct ch ...

ammonia
. Conversely, neutralizing a weak acid with a strong base gives a weakly basic salt, e.g.
sodium fluoride Sodium fluoride (NaF) is an inorganic compound with the formula . It is used in trace amounts in the fluoridation of drinking water, in toothpaste, in metallurgy, and as a flux (metallurgy), flux, and is also used in pesticides and rat poison. It i ...

sodium fluoride
from
hydrogen fluoride Hydrogen fluoride is a chemical compound with the chemical formula . This colorless gas or liquid is the principal industrial source of fluorine, often as an aqueous solution called hydrofluoric acid. It is an important feedstock in the preparation ...

hydrogen fluoride
and
sodium hydroxide Sodium hydroxide, also known as lye A lye is a metal hydroxide traditionally obtained by leaching wood ashes, or a strong alkali In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chem ...

sodium hydroxide
.


Weak acid–weak base equilibrium

In order for a protonated acid to lose a proton, the pH of the system must rise above the p''K''a of the acid. The decreased concentration of H+ in that basic solution shifts the equilibrium towards the conjugate base form (the deprotonated form of the acid). In lower-pH (more acidic) solutions, there is a high enough H+ concentration in the solution to cause the acid to remain in its protonated form. Solutions of weak acids and salts of their conjugate bases form
buffer solution A buffer solution (more precisely, pH buffer or hydrogen ion buffer) is an aqueous solution consisting of a mixture of a weak acid and its conjugate base, or vice versa. Its pH changes very little when a small amount of strong acid or Base (chemistr ...
s.


Titration

To determine the concentration of an acid in an aqueous solution, an acid–base titration is commonly performed. A strong base solution with a known concentration, usually NaOH or KOH, is added to neutralize the acid solution according to the color change of the indicator with the amount of base added. The titration curve of an acid titrated by a base has two axes, with the base volume on the x-axis and the solution's pH value on the y-axis. The pH of the solution always goes up as the base is added to the solution.


Example: Diprotic acid

For each diprotic acid titration curve, from left to right, there are two midpoints, two equivalence points, and two buffer regions.


Equivalence points

Due to the successive dissociation processes, there are two equivalence points in the titration curve of a diprotic acid. The first equivalence point occurs when all first hydrogen ions from the first ionization are titrated. In other words, the amount of OH added equals the original amount of H2A at the first equivalence point. The second equivalence point occurs when all hydrogen ions are titrated. Therefore, the amount of OH added equals twice the amount of H2A at this time. For a weak diprotic acid titrated by a strong base, the second equivalence point must occur at pH above 7 due to the hydrolysis of the resulted salts in the solution. At either equivalence point, adding a drop of base will cause the steepest rise of the pH value in the system.


Buffer regions and midpoints

A titration curve for a diprotic acid contains two midpoints where pH=pKa. Since there are two different Ka values, the first midpoint occurs at pH=pKa1 and the second one occurs at pH=pKa2. Each segment of the curve which contains a midpoint at its center is called the buffer region. Because the buffer regions consist of the acid and its conjugate base, it can resist pH changes when base is added until the next equivalent points.


Applications of acids

Acids exist universally in our life. There are both numerous kinds of natural acid compounds with biological functions and massive synthesized acids which are used in many ways.


In industry

Acids are fundamental reagents in treating almost all processes in today's industry. Sulfuric acid, a diprotic acid, is the most widely used acid in industry, which is also the most-produced industrial chemical in the world. It is mainly used in producing fertilizer, detergent, batteries and dyes, as well as used in processing many products such like removing impurities. According to the statistics data in 2011, the annual production of sulfuric acid was around 200 million tonnes in the world. For example, phosphate minerals react with sulfuric acid to produce
phosphoric acid Phosphoric acid, also known as orthophosphoric acid or phosphoric(V) acid, is a weak acid with the chemical formula . The pure compound is a colorless solid. All three hydrogens are acidic to varying degrees and can be lost from the molecule ...

phosphoric acid
for the production of phosphate fertilizers, and
zinc Zinc is a chemical element In chemistry, an element is a pure Chemical substance, substance consisting only of atoms that all have the same numbers of protons in their atomic nucleus, nuclei. Unlike chemical compounds, chemical element ...

zinc
is produced by dissolving zinc oxide into sulfuric acid, purifying the solution and electrowinning. In the chemical industry, acids react in neutralization reactions to produce salts. For example,
nitric acid Nitric acid (), also known as ''aqua fortis'' (Latin for "strong water") and spirit of niter, is a highly corrosive mineral acid. The pure compound is colorless, but older samples tend to acquire a yellow cast due to decomposition into nitroge ...

nitric acid
reacts with
ammonia Ammonia is a chemical compound, compound of nitrogen and hydrogen with the chemical formula, formula NH3. A Binary compounds of hydrogen, stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct ch ...

ammonia
to produce
ammonium nitrate Ammonium nitrate is a chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entity, molecular entities) composed of atoms from more than one chemical element, element held together ...

ammonium nitrate
, a fertilizer. Additionally,
carboxylic acid A carboxylic acid is an organic acid that contains a carboxyl group (C(=O)OH) attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with substituent, R referring to the alkyl, alkenyl, aryl, or other group. ...
s can be
esterified An ester is a chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entity, molecular entities) composed of atoms from more than one chemical element, element held together by chemical ...

esterified
with alcohols, to produce
ester An ester is a chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entity, molecular entities) composed of atoms from more than one chemical element, element held together by chemic ...

ester
s. Acids are often used to remove rust and other corrosion from metals in a process known as
pickling Pickling is the process of preserving or extending the shelf life of food Food is any substance consumed to provide Nutrient, nutritional support for an organism. Food is usually of plant, animal or Fungus, fungal origin, and contains ess ...
. They may be used as an electrolyte in a wet cell battery, such as
sulfuric acid Sulfuric acid (American spelling Despite the various English dialects spoken from country to country and within different regions of the same country, there are only slight regional variations in English orthography English orthogra ...

sulfuric acid
in a
car battery An automotive battery or car battery is a rechargeable battery A rechargeable battery, storage battery, or secondary cell, (or archaically accumulator) is a type of electrical battery A battery is a device consisting of one or more ...
.


In food

Tartaric acid Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in bananas, tamarinds, and citrus. Its salt (chemistry), salt, potassium bitartrate, commonly known as cream of tartar, dev ...

Tartaric acid
is an important component of some commonly used foods like unripened mangoes and tamarind. Natural fruits and vegetables also contain acids.
Citric acid Citric acid is an organic compound In , organic compounds are generally any s that contain - . Due to carbon's ability to (form chains with other carbon s), millions of organic compounds are known. The study of the properties, reactions, ...

Citric acid
is present in oranges, lemon and other citrus fruits.
Oxalic acid Oxalic acid is an organic acid An organic acid is an with ic properties. The most common organic acids are the s, whose acidity is associated with their  –COOH. s, containing the group –SO2OH, are relatively stronger acids. Alcoh ...

Oxalic acid
is present in tomatoes, spinach, and especially in
carambola Carambola, also known as star fruit or starfruit, is the fruit of ''Averrhoa carambola ''Averrhoa carambola'' is a species of tree in the family Oxalidaceae native to tropical Southeast Asia; it has a number of common names, including caramb ...
and
rhubarb Rhubarb is the fleshy, edible stalks ( petioles) of species and hybrids (culinary rhubarb) of '' Rheum'' in the family Polygonaceae The Polygonaceae are a family In human society A society is a Social group, group of individuals ...

rhubarb
; rhubarb leaves and unripe carambolas are toxic because of high concentrations of oxalic acid.
Ascorbic acid Vitamin C (also known as ascorbic acid and ascorbate) is a vitamin A vitamin is an organic molecule , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carb ...

Ascorbic acid
(Vitamin C) is an essential vitamin for the human body and is present in such foods as amla (
Indian gooseberry ''Phyllanthus emblica'', also known as emblic, emblic myrobalan, myrobalan, Indian gooseberry, Malacca tree, or amla from Sanskrit amalaki is a deciduous In the fields of horticulture and botany, the term ''deciduous'' (; ) means "falling off ...
), lemon, citrus fruits, and guava. Many acids can be found in various kinds of food as additives, as they alter their taste and serve as preservatives.
Phosphoric acid Phosphoric acid, also known as orthophosphoric acid or phosphoric(V) acid, is a weak acid with the chemical formula . The pure compound is a colorless solid. All three hydrogens are acidic to varying degrees and can be lost from the molecule ...

Phosphoric acid
, for example, is a component of
cola Cola is a carbonated Carbonation is the chemical reaction A chemical reaction is a process that leads to the chemical transformation of one set of chemical substances to another. Classically, chemical A chemical substance is a form of ...

cola
drinks.
Acetic acid Acetic acid , systematically named ethanoic acid , is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is no less than 4% acetic acid by volume, making acetic acid ...

Acetic acid
is used in day-to-day life as vinegar. Citric acid is used as a preservative in sauces and pickles.
Carbonic acid In chemistry, carbonic acid is a dibasic acid with the chemical formula A chemical formula is a way of presenting information about the chemical proportions of s that constitute a particular or molecule, using symbols, numbers, and s ...

Carbonic acid
is one of the most common acid additives that are widely added in
soft drink A soft drink (see #Terminology, § Terminology for other names) is a drink that usually contains water (often Carbonated water, carbonated), a Sweetness, sweetener, and a natural and/or Artificial Flavoring, artificial flavoring. The sweetene ...

soft drink
s. During the manufacturing process, CO2 is usually pressurized to dissolve in these drinks to generate carbonic acid. Carbonic acid is very unstable and tends to decompose into water and CO2 at room temperature and pressure. Therefore, when bottles or cans of these kinds of soft drinks are opened, the soft drinks fizz and effervesce as CO2 bubbles come out. Certain acids are used as drugs.
Acetylsalicylic acid Aspirin, also known as acetylsalicylic acid (ASA), is a medication A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to medical diagnosis, diagnose, cure, therapy, treat, ...
(Aspirin) is used as a pain killer and for bringing down fevers.


In human bodies

Acids play important roles in the human body. The hydrochloric acid present in the stomach aids digestion by breaking down large and complex food molecules. Amino acids are required for synthesis of proteins required for growth and repair of body tissues. Fatty acids are also required for growth and repair of body tissues. Nucleic acids are important for the manufacturing of DNA and RNA and transmitting of traits to offspring through genes. Carbonic acid is important for maintenance of pH equilibrium in the body. Human bodies contain a variety of organic and inorganic compounds, among those
dicarboxylic acidA dicarboxylic acid is an organic compound , CH4; is among the simplest organic compounds. In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecul ...
s play an essential role in many biological behaviors. Many of those acids are
amino acids Amino acids are organic compound In , organic compounds are generally any s that contain - . Due to carbon's ability to (form chains with other carbon s), millions of organic compounds are known. The study of the properties, reactions, a ...

amino acids
which mainly serve as materials for the synthesis of proteins. Other weak acids serve as buffers with their conjugate bases to keep the body's pH from undergoing large scale changes which would be harmful to cells. The rest of the dicarboxylic acids also participate in the synthesis of various biologically important compounds in human bodies.


Acid catalysis

Acids are used as
catalyst Catalysis () is the process of increasing the rate of a chemical reaction A chemical reaction is a process that leads to the chemical transformation of one set of chemical substance A chemical substance is a form of matter In cla ...

catalyst
s in industrial and organic chemistry; for example,
sulfuric acid Sulfuric acid (American spelling Despite the various English dialects spoken from country to country and within different regions of the same country, there are only slight regional variations in English orthography English orthogra ...

sulfuric acid
is used in very large quantities in the
alkylation Alkylation is the transfer of an alkyl In organic chemistry, an alkyl substituent is an alkane missing one hydrogen. The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of ...

alkylation
process to produce gasoline. Some acids, such as sulfuric, phosphoric, and hydrochloric acids, also effect
dehydration In physiology, dehydration is a lack of total body water In physiology Physiology (; ) is the scientific study of functions and mechanisms in a living system. As a sub-discipline of biology Biology is the natural science that studie ...
and
condensation reaction In , a condensation reaction is a type of in which two s are to form a single molecule, usually with the loss of a small molecule such as . If water is lost, the reaction is also known as a . However other molecules can also be lost, such as , , ...
s. In biochemistry, many
enzyme Enzymes () are proteins that act as biological catalysts (biocatalysts). Catalysts accelerate chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates in ...

enzyme
s employ acid catalysis.


Biological occurrence

Many biologically important molecules are acids.
Nucleic acid Nucleic acids are biopolymer Biopolymers are natural polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material consisting of very large molecules, or macromolecule ...

Nucleic acid
s, which contain acidic , include
DNA Deoxyribonucleic acid (; DNA) is a molecule A scanning tunneling microscopy image of pentacene molecules, which consist of linear chains of five carbon rings. A molecule is an electrically Electricity is the set of physical ...

DNA
and
RNA Ribonucleic acid (RNA) is a polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material consisting of very large molecules, or macromolecules, composed of many Re ...

RNA
. Nucleic acids contain the genetic code that determines many of an organism's characteristics, and is passed from parents to offspring. DNA contains the chemical blueprint for the synthesis of
protein Proteins are large biomolecule , showing alpha helices, represented by ribbons. This poten was the first to have its suckture solved by X-ray crystallography by Max Perutz and Sir John Cowdery Kendrew in 1958, for which they received a No ...

protein
s which are made up of
amino acid Amino acids are organic compound In , organic compounds are generally any s that contain - . Due to carbon's ability to (form chains with other carbon s), millions of organic compounds are known. The study of the properties, reactions, a ...

amino acid
subunits.
Cell membrane The cell membrane (also known as the plasma membrane (PM) or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane A biological membrane, biomembrane or cell membrane is a selectively permeable membra ...

Cell membrane
s contain
fatty acid In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during ...
ester An ester is a chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entity, molecular entities) composed of atoms from more than one chemical element, element held together by chemic ...

ester
s such as
phospholipids Phospholipids, also known as phosphatides, are a class of lipids whose molecule has a hydrophile, hydrophilic "head" containing a phosphate group and two hydrophobic "tails" derived from fatty acids, joined by an alcohol residue (usually a glyce ...

phospholipids
. An α-amino acid has a central carbon (the α or ''alpha'' carbon) which is covalently bonded to a
carboxyl A carboxylic acid is an organic acid An organic acid is an organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: th ...

carboxyl
group (thus they are
carboxylic acid A carboxylic acid is an organic acid that contains a carboxyl group (C(=O)OH) attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with substituent, R referring to the alkyl, alkenyl, aryl, or other group. ...
s), an
amino In organic chemistry Organic chemistry is a branch of chemistry that studies the structure, properties and reactions of organic compounds, which contain carbon in covalent bonding.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemi ...

amino
group, a hydrogen atom and a variable group. The variable group, also called the R group or side chain, determines the identity and many of the properties of a specific amino acid. In
glycine Glycine (symbol Gly or G; ) is an amino acid Amino acids are organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond ...

glycine
, the simplest amino acid, the R group is a hydrogen atom, but in all other amino acids it is contains one or more carbon atoms bonded to hydrogens, and may contain other elements such as sulfur, oxygen or nitrogen. With the exception of glycine, naturally occurring amino acids are
chiral Chirality is a property of asymmetry Asymmetry is the absence of, or a violation of, symmetry (the property of an object being invariant to a transformation, such as reflection). Symmetry is an important property of both physical and abstrac ...
and almost invariably occur in the L-configuration.
Peptidoglycan Peptidoglycan or murein is a polymer A polymer (; Greek ''poly- Poly, from the Greek :wikt:πολύς, πολύς meaning "many" or "much", may refer to: Businesses * China Poly Group Corporation, a Chinese business group, and its subsidia ...

Peptidoglycan
, found in some bacterial
cell wall A cell wall is a structural layer surrounding some types of cells, just outside the cell membrane cell membrane vs. Prokaryotes The cell membrane (also known as the plasma membrane (PM) or cytoplasmic membrane, and historically referred to a ...
s contains some D-amino acids. At physiological pH, typically around 7, free amino acids exist in a charged form, where the acidic carboxyl group (-COOH) loses a proton (-COO) and the basic amine group (-NH2) gains a proton (-NH). The entire molecule has a net neutral charge and is a
zwitterionIn chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they undergo ...
, with the exception of amino acids with basic or acidic side chains. Aspartic acid, for example, possesses one protonated amine and two deprotonated carboxyl groups, for a net charge of −1 at physiological pH. Fatty acids and fatty acid derivatives are another group of carboxylic acids that play a significant role in biology. These contain long hydrocarbon chains and a carboxylic acid group on one end. The cell membrane of nearly all organisms is primarily made up of a
phospholipid bilayer The lipid bilayer (or phospholipid bilayer) is a thin polar membrane A polarized membrane is a lipid bilayer, lipid membrane that has a positive electrical charge on one side and a negative charge on another side, which produces the resting pote ...
, a
micelle Image:Micelle scheme-en.svg, 250px, Scheme of a micelle formed by phospholipids in an aqueous solution A micelle () or micella () (plural micelles or micellae, respectively) is an aggregate (or supramolecular assembly) of surfactant phospholipid ...

micelle
of hydrophobic fatty acid esters with polar, hydrophilic
phosphate In chemistry, a phosphate is an anion, salt (chemistry), salt, functional group or ester derived from a phosphoric acids and phosphates, phosphoric acid. It most commonly means orthophosphate, a derivative of phosphoric acid, orthophosphoric a ...

phosphate
"head" groups. Membranes contain additional components, some of which can participate in acid–base reactions. In humans and many other animals,
hydrochloric acid Hydrochloric acid +(aq) Cl−(aq) or H3O+ Cl− also known as muriatic acid, is an aqueous solution An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a salin ...

hydrochloric acid
is a part of the
gastric acid Gastric acid, gastric juice, or stomach acid, is a digestive fluid formed within the stomach lining. With a pH between 1 and 3, gastric acid An acid is a or capable of donating a (hydrogen ion H+) (a ), or, alternatively, capable of for ...
secreted within the
stomach The stomach is a muscular, in the of humans and many other animals, including several s. The stomach has a dilated structure and functions as a vital organ. In the digestive system the stomach is involved in the second phase of digestion, ...

stomach
to help hydrolyze
protein Proteins are large biomolecule , showing alpha helices, represented by ribbons. This poten was the first to have its suckture solved by X-ray crystallography by Max Perutz and Sir John Cowdery Kendrew in 1958, for which they received a No ...

protein
s and
polysaccharide Polysaccharides (), or polycarbohydrates, are the most abundant carbohydrate A carbohydrate () is a biomolecule , showing alpha helices, represented by ribbons. This poten was the first to have its suckture solved by X-ray crystallograp ...
s, as well as converting the inactive pro-enzyme,
pepsinogen Pepsin is an endopeptidase that breaks down protein Proteins are large biomolecules or macromolecules that are comprised of one or more long chains of amino acid residue (biochemistry), residues. Proteins perform a vast array of functions w ...
into the
enzyme Enzymes () are proteins that act as biological catalysts (biocatalysts). Catalysts accelerate chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates in ...
,
pepsin Pepsin is an endopeptidase that breaks down proteins into smaller peptides. It is produced in the gastric chief cells of the stomach lining and is one of the main digestive enzymes in the digestive systems of humans and many other animals, where ...

pepsin
. Some organisms produce acids for defense; for example, ants produce
formic acid Formic acid, systematically named methanoic acid, is the simplest carboxylic acid A carboxylic acid is an organic acid An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acid ...

formic acid
. Acid–base equilibrium plays a critical role in regulating
mammal Mammals (from Latin Latin (, or , ) is a classical language A classical language is a language A language is a structured system of communication Communication (from Latin ''communicare'', meaning "to share" or "to be i ...
ian breathing.
Oxygen Oxygen is the chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the chemical elements In chemistry, an element is a pure substance consisting only of atoms that all have the same ...

Oxygen
gas (O2) drives
cellular respiration Cellular respiration is a set of metabolic Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life Life is a characteristic that distinguishes physical entities that have biological processes, such a ...

cellular respiration
, the process by which animals release the chemical
potential energy In physics, potential energy is the energy In , energy is the that must be to a or to perform on the body, or to it. Energy is a ; the law of states that energy can be in form, but not created or destroyed. The unit of measure ...

potential energy
stored in food, producing
carbon dioxide Carbon dioxide (chemical formula A chemical formula is a way of presenting information about the chemical proportions of s that constitute a particular or molecule, using symbols, numbers, and sometimes also other symbols, such as pare ...

carbon dioxide
(CO2) as a byproduct. Oxygen and carbon dioxide are exchanged in the
lungs The lungs are the primary organs of the respiratory system The respiratory system (also respiratory apparatus, ventilatory system) is a biological system consisting of specific organs and structures used for gas exchange in animal ...

lungs
, and the body responds to changing energy demands by adjusting the rate of
ventilation Ventilation may refer to: * Ventilation (physiology), the movement of air between the environment and the lungs via inhalation and exhalation ** Mechanical ventilation, in medicine, using artificial methods to assist breathing *** Ventilator, a mac ...
. For example, during periods of exertion the body rapidly breaks down stored
carbohydrate A carbohydrate () is a biomolecule , showing alpha helices, represented by ribbons. This poten was the first to have its suckture solved by X-ray crystallography by Max Perutz and Sir John Cowdery Kendrew in 1958, for which they received a ...
s and fat, releasing CO2 into the blood stream. In aqueous solutions such as blood CO2 exists in equilibrium with
carbonic acid In chemistry, carbonic acid is a dibasic acid with the chemical formula A chemical formula is a way of presenting information about the chemical proportions of s that constitute a particular or molecule, using symbols, numbers, and s ...

carbonic acid
and
bicarbonate In inorganic chemistry, bicarbonate (International Union of Pure and Applied Chemistry, IUPAC-recommended nomenclature: hydrogen carbonate) is an intermediate form in the deprotonation of carbonic acid. It is a Polyatomic ion, polyatomic anion w ...

bicarbonate
ion. : CO2 + H2O H2CO3 H+ + HCO It is the decrease in pH that signals the brain to breathe faster and deeper, expelling the excess CO2 and resupplying the cells with O2.
Cell membrane The cell membrane (also known as the plasma membrane (PM) or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane A biological membrane, biomembrane or cell membrane is a selectively permeable membra ...

Cell membrane
s are generally impermeable to charged or large, polar molecules because of the
lipophilicLipophilicity (from Greek language, Greek λίπος "fat" and :wikt:φίλος, φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar ...
fatty acyl chains comprising their interior. Many biologically important molecules, including a number of pharmaceutical agents, are organic weak acids which can cross the membrane in their protonated, uncharged form but not in their charged form (i.e. as the conjugate base). For this reason the activity of many drugs can be enhanced or inhibited by the use of antacids or acidic foods. The charged form, however, is often more soluble in blood and
cytosol The cytosol, also known as cytoplasmic matrix or groundplasm, is one of the liquids found inside cells Cell most often refers to: * Cell (biology), the functional basic unit of life Cell may also refer to: Closed spaces * Monastic cell, a s ...
, both aqueous environments. When the extracellular environment is more acidic than the neutral pH within the cell, certain acids will exist in their neutral form and will be membrane soluble, allowing them to cross the phospholipid bilayer. Acids that lose a proton at the
intracellular pH Intracellular pH (pHi) is the measure of the acidity An acid is a molecule A molecule is an electrically Electricity is the set of physical phenomena associated with the presence and motion Image:Leaving Yongsan Station.j ...
will exist in their soluble, charged form and are thus able to diffuse through the cytosol to their target.
Ibuprofen Ibuprofen is a medication in the nonsteroidal anti-inflammatory drug (NSAID) class that is used for treating pain, fever, and inflammation. This includes dysmenorrhea, painful menstrual periods, migraines, and rheumatoid arthritis. It may also ...

Ibuprofen
,
aspirin Aspirin, also known as acetylsalicylic acid (ASA), is a medication used to reduce pain, fever, or inflammation. Specific inflammatory conditions which aspirin is used to treat include Kawasaki disease, pericarditis, and rheumatic fever. Aspirin ...

aspirin
and
penicillin Penicillins (P, PCN or PEN) are a group of antibiotics An antibiotic is a type of antimicrobial An antimicrobial is an agent that kills microorganism A microorganism, or microbe,, ''mikros'', "small") and ''organism ...

penicillin
are examples of drugs that are weak acids.


Common acids


Mineral acids (inorganic acids)

* Hydrogen halides and their solutions:
hydrofluoric acid Hydrofluoric acid is a Solution (chemistry), solution of hydrogen fluoride (HF) in water. Solutions of HF are colourless, acidic and highly Corrosive substance, corrosive. It is used to make most fluorine-containing compounds; examples include th ...
(HF),
hydrochloric acid Hydrochloric acid +(aq) Cl−(aq) or H3O+ Cl− also known as muriatic acid, is an aqueous solution An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a salin ...

hydrochloric acid
(HCl),
hydrobromic acid Hydrobromic acid is a strong acid Acid strength is the tendency of an acid An acid is a or capable of donating a (hydrogen ion H+) (a ), or, alternatively, capable of forming a with an (a ). The first category of acids are the pr ...

hydrobromic acid
(HBr),
hydroiodic acid Hydroiodic acid (or hydriodic acid) is an aqueous solution An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a saline water solution by dissolving Salt, table sa ...
(HI) * Halogen oxoacids:
hypochlorous acid Hypochlorous acid (HOCl or HClO) is a weak acid An acid is a molecule or ion capable of donating a proton (hydrogen ion H+) (a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid), or, alternatively, capable of forming a covalent bo ...
(HClO),
chlorous acid Chlorous acid is an inorganic compound In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: their composition, structure, propert ...
(HClO2), (HClO3),
perchloric acid Perchloric acid is a mineral acid A mineral acid (or inorganic acid) is an acid An acid is a molecule or ion An ion () is a particle In the Outline of physical science, physical sciences, a particle (or corpuscule in older texts) ...
(HClO4), and corresponding analogs for bromine and iodine **
Hypofluorous acid Hypofluorous acid, chemical formula A chemical formula is a way of presenting information about the chemical proportions of s that constitute a particular or molecule, using symbols, numbers, and sometimes also other symbols, such as paren ...

Hypofluorous acid
(HFO), the only known oxoacid for fluorine. *
Sulfuric acid Sulfuric acid (American spelling Despite the various English dialects spoken from country to country and within different regions of the same country, there are only slight regional variations in English orthography English orthogra ...

Sulfuric acid
(H2SO4) *
Fluorosulfuric acid Fluorosulfuric acid (IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations that represents chemists in individual countries. It is a member of the International S ...
(HSO3F) *
Nitric acid Nitric acid (), also known as ''aqua fortis'' (Latin for "strong water") and spirit of niter, is a highly corrosive mineral acid. The pure compound is colorless, but older samples tend to acquire a yellow cast due to decomposition into nitroge ...

Nitric acid
(HNO3) *
Phosphoric acid Phosphoric acid, also known as orthophosphoric acid or phosphoric(V) acid, is a weak acid with the chemical formula . The pure compound is a colorless solid. All three hydrogens are acidic to varying degrees and can be lost from the molecule ...

Phosphoric acid
(H3PO4) *
Fluoroantimonic acid Fluoroantimonic acid is a mixture of hydrogen fluoride and antimony pentafluoride, containing various cations and anions (the simplest being and ). This substance is a superacid, that can be over a billion times stronger than 100% pure sulfuric ...

Fluoroantimonic acid
(HSbF6) *
Fluoroboric acid Fluoroboric acid or tetrafluoroboric acid (archaically, fluoboric acid) is an inorganic compound In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, ...

Fluoroboric acid
(HBF4) *
Hexafluorophosphoric acid Hexafluorophosphoric acid is the inorganic compound In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: their composition, struc ...
(HPF6) *
Chromic acid The term chromic acid is usually used for a mixture made by adding concentrated sulfuric acid Sulfuric acid ( American spelling) or sulphuric acid ( Commonwealth spelling), also known as oil of vitriol, is a mineral acid composed of the elem ...
(H2CrO4) *
Boric acid Boric acid, also called hydrogen borate, boracic acid, and orthoboric acid is a weak, monobasic Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is ...

Boric acid
(H3BO3)


Sulfonic acids

A
sulfonic acid A sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds Organosulfur compounds are organic compound , CH4; is among the simplest organic compounds. In chemistry Chemistry is the scientific discipline inv ...

sulfonic acid
has the general formula RS(=O)2–OH, where R is an organic radical. *
Methanesulfonic acid Methanesulfonic acid (MsOH) or methanesulphonic acid (in British English) is a colorless liquid with the chemical formula CH3SO3H. It is the simplest of the alkylsulfonic acids. Salts In chemistry, a salt is a chemical compound consisting of a ...

Methanesulfonic acid
(or mesylic acid, CH3SO3H) * Ethanesulfonic acid (or esylic acid, CH3CH2SO3H) *
Benzenesulfonic acid Benzenesulfonic acid (conjugate acid, conjugate base benzenesulfonate) is an organosulfur compound with the formula carbon, C6hydrogen, H6oxygen, O3sulfur, S. It is the simplest aromaticity, aromatic sulfonic acid. It forms white deliquescent sheet ...

Benzenesulfonic acid
(or besylic acid, C6H5SO3H) *
p-Toluenesulfonic acid ''p''-Toluenesulfonic acid (PTSA or ''p''TsOH) or tosylic acid (TsOH) is an organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemic ...

p-Toluenesulfonic acid
(or tosylic acid, CH3C6H4SO3H) *
Trifluoromethanesulfonic acid Triflic acid, is the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest acid (chemistry), acids. Triflic acid is mainly used in research as a ca ...
(or triflic acid, CF3SO3H) * Polystyrene sulfonic acid (sulfonated
polystyrene Polystyrene (PS) is a synthetic Aromaticity, aromatic hydrocarbon polymer made from the monomer known as styrene. Polystyrene can be solid or foamed. General-purpose polystyrene is clear, hard, and brittle. It is an inexpensive resin per un ...

polystyrene
, H2CH(C6H4)SO3Hsub>n)


Carboxylic acids

A
carboxylic acid A carboxylic acid is an organic acid that contains a carboxyl group (C(=O)OH) attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with substituent, R referring to the alkyl, alkenyl, aryl, or other group. ...
has the general formula R-C(O)OH, where R is an organic radical. The carboxyl group -C(O)OH contains a
carbonyl In organic chemistry Organic chemistry is a branch of chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, pro ...

carbonyl
group, C=O, and a
hydroxyl A hydroxy or hydroxyl group is a functional group with the chemical formula -OH and composed of one oxygen Oxygen is the chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the ...

hydroxyl
group, O-H. *
Acetic acid Acetic acid , systematically named ethanoic acid , is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is no less than 4% acetic acid by volume, making acetic acid ...

Acetic acid
(CH3COOH) *
Citric acid Citric acid is an organic compound In , organic compounds are generally any s that contain - . Due to carbon's ability to (form chains with other carbon s), millions of organic compounds are known. The study of the properties, reactions, ...

Citric acid
(C6H8O7) *
Formic acid Formic acid, systematically named methanoic acid, is the simplest carboxylic acid A carboxylic acid is an organic acid An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acid ...

Formic acid
(HCOOH) *
Gluconic acid Gluconic acid is an organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to Catenation, c ...

Gluconic acid
HOCH2-(CHOH)4-COOH *
Lactic acid Lactic acid is an organic acid An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids, whose acidity is associated with their carboxyl group –COOH. Sulfonic acids, conta ...

Lactic acid
(CH3-CHOH-COOH) *
Oxalic acid Oxalic acid is an organic acid An organic acid is an with ic properties. The most common organic acids are the s, whose acidity is associated with their  –COOH. s, containing the group –SO2OH, are relatively stronger acids. Alcoh ...

Oxalic acid
(HOOC-COOH) *
Tartaric acid Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in bananas, tamarinds, and citrus. Its salt (chemistry), salt, potassium bitartrate, commonly known as cream of tartar, dev ...

Tartaric acid
(HOOC-CHOH-CHOH-COOH)


Halogenated carboxylic acids

Halogenation at alpha position increases acid strength, so that the following acids are all stronger than acetic acid. *
Fluoroacetic acid Fluoroacetic acid is a organofluorine compound B: isoflurane Isoflurane, sold under the brand name Forane among others, is a general anesthetic. It can be used to start or maintain anesthesia, however other medications are often used to start a ...

Fluoroacetic acid
*
Trifluoroacetic acid Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula A chemical formula is a way of presenting information about the chemical proportions of atom An atom is the smallest unit of ordinary matter In cla ...

Trifluoroacetic acid
*
Chloroacetic acid Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds are ...

Chloroacetic acid
* Dichloroacetic acid *
Trichloroacetic acid Trichloroacetic acid (TCA; TCAA; also known as trichloroethanoic acid) is an analogue of acetic acid Acetic acid , systematically named ethanoic acid , is a colourless liquid organic compound , CH4; is among the simplest organic compounds. ...

Trichloroacetic acid


Vinylogous carboxylic acids

Normal carboxylic acids are the direct union of a carbonyl group and a hydroxyl group. In
vinylogousVinylogy is the transmission of electronic effects through a conjugated organic bonding system. The concept was introduced in 1926 by Ludwig Claisen to explain the acidic properties of formylacetone and related ketoaldehydes. Its adjectival form, ...

vinylogous
carboxylic acids, a carbon-carbon double bond separates the carbonyl and hydroxyl groups. *
Ascorbic acid Vitamin C (also known as ascorbic acid and ascorbate) is a vitamin A vitamin is an organic molecule , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carb ...

Ascorbic acid


Nucleic acids

*
Deoxyribonucleic acid Deoxyribonucleic acid (; DNA) is a molecule composed of two polynucleotide chains that coil around each other to form a Nucleic acid double helix, double helix carrying genetics, genetic instructions for the development, functioning, growth ...

Deoxyribonucleic acid
(DNA) *
Ribonucleic acid Ribonucleic acid (RNA) is a polymer A polymer (; Greek '' poly-'', "many" + '' -mer'', "part") is a substance or material consisting of very large molecule File:Pentacene on Ni(111) STM.jpg, A scanning tunneling microscopy image of ...

Ribonucleic acid
(RNA)


References


Listing of strengths of common acids and bases
* *


External links



Acid–Base equilibria diagrams, calculation and
titration Titration (also known as titrimetry and volumetric analysis) is a common laboratory method of quantitative chemical analysis Analytical chemistry studies and uses instruments and methods used to separate, identify, and quantify matter. In pr ...

titration
curves simulation and analysis –
freeware Freeware is software Software is a collection of Instruction (computer science), instructions that tell a computer how to work. This is in contrast to Computer hardware, hardware, from which the system is built and actually performs the work ...

freeware
{{Authority control Acid–base chemistry