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Do Carbenes Have a “Hidden” Carbon(0) Character? Revisiting the Electronic Structure of 2,2′‐Bipyridyl Carbene
Author(s) -
Guha Ankur Kanti,
Phukan Ashwini K.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103250
Subject(s) - carbene , character (mathematics) , dissociation (chemistry) , chemistry , proton affinity , bond dissociation energy , density functional theory , molecule , carbon fibers , computational chemistry , transition metal carbene complex , photochemistry , crystallography , organic chemistry , materials science , catalysis , mathematics , ion , geometry , protonation , composite number , composite material
Density functional calculations predict that 2,2′‐bipyridyl carbenes have some degree of “hidden” carbon(0) character. This is supported by very high second proton affinity values and bond dissociation energies (BDEs) for the dissociation of one AuCl and one Ni(CO) 2 molecule from [(AuCl) 2 (2,2′‐bipyridyl carbene)] and [{Ni(CO) 2 } 2 (2,2′‐bipyridyl carbene)]. An Arduengo type carbene also showed significant BDE values for gem‐dimetallation, thus indicating the possible existence of carbon(0) character. All of the dimetallated derivatives showed metallophilic interactions.