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Organocopper chemistry
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Organocopper chemistry
Organocopper chemistry is the study of the physical properties, reactions, and synthesis of organocopper compounds, which are organometallic compounds containing a carbon to copper chemical bond. 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:
Organocopper compounds are diverse in structure and reactivity, but almost all are based on copper with an oxidation state of +1, sometimes denoted Cu(I) or Cu+. With 10 electrons in its valence shell, the bonding behavior of Cu(I) is similar to Ni(0), but owing to its higher oxidation state, it engages in less pi-backbonding. Organic derivatives of copper's higher oxidation states of +2 and +3 are sometimes encountered as reaction intermediates, but rarely isolated or even observed.
Organocopper compounds form complexes with a variety of soft ligands such as alkylphosphines (R3P), thioethers (R2S), and cyanide (CN−).
Due to the spherical electronic shell of Cu+, copper(I) complexes have symmetrical structures - either linear, trigonal planar or tetrahedral, depending on the number of ligands.
Copper(I) salts have long been known to bind CO, albeit weakly. A representative complex is carbonylcopper(I) chloride CuCl(CO), which is polymeric. In contrast to classical metal carbonyls, pi backbonding is not strong in these compounds.
Alkenes bind to copper(I), although again generally weakly. The binding of ethylene to Cu in proteins has a broad significance in plant biology so much so that ethylene is classified as a plant hormone. Its presence, detected by the Cu-protein, affects fruit ripening and many other developments.
Copper forms no metallocene, and adds cyclopentadiene only in the presence of "soft" Lewis bases to give half-sandwich complexes. One such derivative is π-cyclopentadienyl(triethylphosphine)copper(I), [C5H5]−[Cu(P(CH2CH3)3)]+.
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Organocopper chemistry
Organocopper chemistry is the study of the physical properties, reactions, and synthesis of organocopper compounds, which are organometallic compounds containing a carbon to copper chemical bond. 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:
Organocopper compounds are diverse in structure and reactivity, but almost all are based on copper with an oxidation state of +1, sometimes denoted Cu(I) or Cu+. With 10 electrons in its valence shell, the bonding behavior of Cu(I) is similar to Ni(0), but owing to its higher oxidation state, it engages in less pi-backbonding. Organic derivatives of copper's higher oxidation states of +2 and +3 are sometimes encountered as reaction intermediates, but rarely isolated or even observed.
Organocopper compounds form complexes with a variety of soft ligands such as alkylphosphines (R3P), thioethers (R2S), and cyanide (CN−).
Due to the spherical electronic shell of Cu+, copper(I) complexes have symmetrical structures - either linear, trigonal planar or tetrahedral, depending on the number of ligands.
Copper(I) salts have long been known to bind CO, albeit weakly. A representative complex is carbonylcopper(I) chloride CuCl(CO), which is polymeric. In contrast to classical metal carbonyls, pi backbonding is not strong in these compounds.
Alkenes bind to copper(I), although again generally weakly. The binding of ethylene to Cu in proteins has a broad significance in plant biology so much so that ethylene is classified as a plant hormone. Its presence, detected by the Cu-protein, affects fruit ripening and many other developments.
Copper forms no metallocene, and adds cyclopentadiene only in the presence of "soft" Lewis bases to give half-sandwich complexes. One such derivative is π-cyclopentadienyl(triethylphosphine)copper(I), [C5H5]−[Cu(P(CH2CH3)3)]+.
