An organic base is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

which acts as a base. Organic bases are usually, but not always, proton acceptors. They usually contain

nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...

atoms, which can easily be protonated. For example, amines or nitrogen-containing heterocyclic compounds have a lone pair of electrons on the nitrogen atom and can thus act as proton acceptors. Examples include: *

pyridine Pyridine is a basic (chemistry), basic heterocyclic compound, heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom . It is a highly flammable, weak ...

* alkylamines, such as methylamine *

imidazole Imidazole (ImH) is an organic compound with the formula . It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. It can be classified as a heterocycle, specifically as a diazole. Many natural products, ...

benzimidazole Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound may be viewed as fused rings of the aromatic compounds benzene and imidazole. It is a white solid that appears in form of tabular crystals. Preparation Benzimi ...

histidine Histidine (symbol His or H) is an essential amino acid that is used in the biosynthesis of proteins. It contains an Amine, α-amino group (which is in the protonated –NH3+ form under Physiological condition, biological conditions), a carboxylic ...

guanidine Guanidine is the compound with the formula HNC(NH2)2. It is a colourless solid that dissolves in polar solvents. It is a strong base that is used in the production of plastics and explosives. It is found in urine predominantly in patients experi ...

* phosphazene bases *

hydroxide Hydroxide is a diatomic anion with chemical formula OH−. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water. It ...

s of quaternary ammonium cations or some other organic cations

Factors affecting alkalinity

Most organic bases are considered to be

weak Weak may refer to: Songs * Weak (AJR song), "Weak" (AJR song), 2016 * Weak (Melanie C song), "Weak" (Melanie C song), 2011 * Weak (SWV song), "Weak" (SWV song), 1993 * Weak (Skunk Anansie song), "Weak" (Skunk Anansie song), 1995 * "Weak", a son ...

. Many factors can affect the strength of the compounds. One such factor is the inductive effect. A simple explanation of the term would state that electropositive atoms (such as carbon groups) attached in close proximity to the potential proton acceptor have an "electron-releasing" effect, such that the positive charge acquired by the proton acceptor is distributed over other adjacent atoms in the chain. The converse is also possible as alleviation of alkalinity: electronegative atoms or species (such as fluorine or the

nitro group In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups (). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nit ...

) will have an "electron-withdrawal" effect and thereby reduce the basicity. To this end,

trimethylamine Trimethylamine (TMA) is an organic compound with the formula N(CH3)3. It is a trimethylated derivative of ammonia. TMA is widely used in industry. At higher concentrations it has an ammonia-like odor, and can cause necrosis of mucous membranes ...

is a more potent base than merely

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

, due to the inductive effect of the

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...

groups allowing the nitrogen atom to more readily accept a proton and become a cation being much greater than that of the hydrogen atoms. In

s, the protonated form ( guanidinium) has three resonance structures, giving it increased stability and making guanidines stronger bases. Phosphazene bases also contain phosphorus and are, in general, more alkaline than standard

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

s and nitrogen-based heterocyclics. Protonation takes place at the nitrogen atom, not the

phosphorus Phosphorus is a chemical element; it has Chemical symbol, symbol P and atomic number 15. All elemental forms of phosphorus are highly Reactivity (chemistry), reactive and are therefore never found in nature. They can nevertheless be prepared ar ...

atom to which the nitrogen is double-bonded.

Hydroxide donors

Some organic bases, such as tetramethylammonium hydroxide, tetrabutylammonium hydroxide, or choline hydroxide are hydroxide donors rather than proton acceptors like the above compounds. However, they are not always stable. Choline hydroxide, for example, is

metastable In chemistry and physics, metastability is an intermediate energetic state within a dynamical system other than the system's state of least energy. A ball resting in a hollow on a slope is a simple example of metastability. If the ball is onl ...

and slowly breaks down to release

References

{{Reflist Bases (chemistry)