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Organocopper
Organocopper compounds is the chemistry of organometallic compounds containing a carbon to copper chemical bond. Organocopper chemistry is the study of organocopper compounds describing their physical properties, synthesis and reactions. They are reagents in organic chemistry. The first organocopper compound, the explosive copper(I) acetylide Cu2C2 (Cu−C≡C−Cu), was synthesized by Rudolf Christian Böttger in 1859 by passing acetylene gas through a solution of copper(I) chloride: :C2H2 + 2 CuCl → Cu2C2 + 2 HCl Structure and bonding Organocopper compounds are diverse in structure and reactivity, but organocopper compounds are largely limited in oxidation states to copper(I), sometimes denoted Cu+. As a d10 metal center, it is related to Ni(0), but owing to its higher oxidation state, it engages in less pi-backbonding. Organic derivatives of Cu(II) and Cu(III) are invoked as intermediates but rarely isolated or even observed. In terms of geometry, copper(I) adopts symmet ...
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Phenylcopper
Phenylcopper is an organometallic chemical compound of copper. Its chemical formula is . Synthesis Phenylcopper was the first known organocopper compound and was first prepared in 1923 from phenylmagnesium iodide and copper(I) iodide and in 1936 by Henry Gilman by transmetallation of phenylmagnesium iodide with copper(I) chloride. Phenylcopper can be obtained by reacting phenyl lithium with copper(I) bromide in diethyl ether. :\mathrm Properties Phenylcopper is a colorless solid substance that is soluble in pyridine. It can be stored for a few days without decomposition under nitrogen or in vacuum. Rapid decomposition takes place in air. Water decomposes phenylcopper to form red copper (I) oxide and varying amounts of benzene and biphenyl. It forms stable complexes with tributylphosphine and triphenylphosphine Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to P Ph3 or Ph3P. It ...
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Copper
Copper is a chemical element with the symbol Cu (from la, cuprum) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkish-orange color. Copper is used as a conductor of heat and electricity, as a building material, and as a constituent of various metal alloys, such as sterling silver used in jewelry, cupronickel used to make marine hardware and coins, and constantan used in strain gauges and thermocouples for temperature measurement. Copper is one of the few metals that can occur in nature in a directly usable metallic form (native metals). This led to very early human use in several regions, from circa 8000 BC. Thousands of years later, it was the first metal to be smelted from sulfide ores, circa 5000 BC; the first metal to be cast into a shape in a mold, c. 4000 BC; and the first metal to be purposely alloyed with another metal, tin, to create br ...
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Organolithium Reagent
In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers. They have also been applied in asymmetric synthesis in the pharmaceutical industry. Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C−Li bond is highly ionic. Owing to the polar nature of the C−Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form. These reagents are highly reactive, and are sometimes pyrophoric. History and d ...
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Copper(I) Chloride
Copper(I) chloride, commonly called cuprous chloride, is the lower chloride of copper, with the formula CuCl. The substance is a white solid sparingly soluble in water, but very soluble in concentrated hydrochloric acid. Impure samples appear green due to the presence of copper(II) chloride (CuCl2). History Copper(I) chloride was first prepared by Robert Boyle in the mid-seventeenth century from mercury(II) chloride ("Venetian sublimate") and copper metal: :HgCl2 + 2 Cu → 2 CuCl + Hg In 1799, J.L. Proust characterized the two different chlorides of copper. He prepared CuCl by heating CuCl2 at red heat in the absence of air, causing it to lose half of its combined chlorine followed by removing residual CuCl2 by washing with water. An acidic solution of CuCl was formerly used for analysis of carbon monoxide content in gases, for example in Hempel's gas apparatus. This application was significant during the nineteenth and early twentieth centuries when coal gas was widel ...
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Group 12 Element
Group 12, by modern IUPAC numbering, is a group of chemical elements in the periodic table. It includes zinc (Zn), cadmium (Cd), mercury (Hg), and copernicium (Cn). Formerly this group was named ''IIB'' (pronounced as "group two B", as the "II" is a Roman numeral) by CAS and old IUPAC system. The three group 12 elements that occur naturally are zinc, cadmium and mercury. They are all widely used in electric and electronic applications, as well as in various alloys. The first two members of the group share similar properties as they are solid metals under standard conditions. Mercury is the only metal that is a liquid at room temperature. While zinc is very important in the biochemistry of living organisms, cadmium and mercury are both highly toxic. As copernicium does not occur in nature, it has to be synthesized in the laboratory. Physical and atomic properties Like other groups of the periodic table, the members of group 12 show patterns in its electron configuration, espe ...
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Electronegativity
Electronegativity, symbolized as , is the tendency for an atom of a given chemical element to attract shared electrons (or electron density) when forming a chemical bond. An atom's electronegativity is affected by both its atomic number and the distance at which its valence electrons reside from the charged nucleus. The higher the associated electronegativity, the more an atom or a substituent group attracts electrons. Electronegativity serves as a simple way to quantitatively estimate the bond energy, and the sign and magnitude of a bond's chemical polarity, which characterizes a bond along the continuous scale from covalent to ionic bonding. The loosely defined term electropositivity is the opposite of electronegativity: it characterizes an element's tendency to donate valence electrons. On the most basic level, electronegativity is determined by factors like the nuclear charge (the more protons an atom has, the more "pull" it will have on electrons) and the number and lo ...
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Functional Group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis. A functional group is a group of atoms in a molecule with distinctive chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their nonpolar core of carbon atoms and thus add chemical character to carbon chains. ...
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Alkylating Reagent
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents. Nucleophilic alkylating agents Nucleophilic alkylating agents deliver the equivalent of an alkyl anion (carbanion). The formal "alkyl anion" attacks an electrophile, forming a new covalent bond ...
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Organic Synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one of the most important branches of organic chemistry. There are several main areas of research within the general area of organic synthesis: '' total synthesis'', '' semisynthesis'', and ''methodology''. Total synthesis A total synthesis is the complete chemical synthesis of complex organic molecules from simple, commercially available petrochemical or natural precursors. Total synthesis may be accomplished either via a linear or convergent approach. In a ''linear'' synthesis—often adequate for simple structures—several steps are performed one after another until the molecule is complete; the chemical compounds made in each step are called synthetic intermediates. Most often, each step in a synthesis refers to a separate ...
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In Situ
''In situ'' (; often not italicized in English) is a Latin phrase that translates literally to "on site" or "in position." It can mean "locally", "on site", "on the premises", or "in place" to describe where an event takes place and is used in many different contexts. For example, in fields such as physics, geology, chemistry, or biology, ''in situ'' may describe the way a measurement is taken, that is, in the same place the phenomenon is occurring without isolating it from other systems or altering the original conditions of the test. The opposite of ''in situ'' is ''ex situ''. Aerospace In the aerospace industry, equipment on-board aircraft must be tested ''in situ'', or in place, to confirm everything functions properly as a system. Individually, each piece may work but interference from nearby equipment may create unanticipated problems. Special test equipment is available for this ''in situ'' testing. It can also refer to repairs made to the aircraft structure or flight ...
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Copper(I) Oxide
Copper(I) oxide or cuprous oxide is the inorganic compound with the formula Cu2O. It is one of the principal oxides of copper, the other being or copper(II) oxide or cupric oxide (CuO). This red-coloured solid is a component of some antifouling paints. The compound can appear either yellow or red, depending on the size of the particles. Copper(I) oxide is found as the reddish mineral cuprite. Preparation Copper(I) oxide may be produced by several methods. Most straightforwardly, it arises via the oxidation of copper metal: : 4 Cu + O2 → 2 Cu2O Additives such as water and acids affect the rate of this process as well as the further oxidation to copper(II) oxides. It is also produced commercially by reduction of copper(II) solutions with sulfur dioxide. Reactions Aqueous cuprous chloride solutions react with base to give the same material. In all cases, the color is highly sensitive to the procedural details. Formation of copper(I) oxide is the basis of the Fehl ...
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