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Reactivity of carbene•phosphine dimers: proton affinity revisited
Author(s) -
Liu Min,
Chen Mu,
Zhang Sisi,
Yang Ill,
Buckley Brian,
Lee Jeehiun K.
Publication year - 2011
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1890
Subject(s) - chemistry , reactivity (psychology) , carbene , phosphine , tricyclohexylphosphine , alkylation , medicinal chemistry , cyclohexene , ethylene , proton affinity , arsine , computational chemistry , organic chemistry , photochemistry , catalysis , protonation , medicine , ion , alternative medicine , pathology
The gas phase reactivity of N ‐heterocyclic carbenes versus tricyclohexylphosphine (PCy 3 ) is examined computationally and experimentally. New measurements indicate that dimethylimidazol‐ and 1‐ethyl‐3‐methylimidazol‐2‐ylidene are more basic than PCy 3 , in contrast to previous measurements made by us and by others. Proton‐bound dimers of the carbenes and PCy 3 are also found to exhibit interesting reactivity involving phosphine alkylation, cyclohexene elimination, and/or ethylene elimination. This novel reactivity is further probed and discussed. Copyright © 2011 John Wiley & Sons, Ltd.