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Revisiting the reactivity of different carbon bases: A theoretical study
Author(s) -
Guha Ankur Kanti,
Gogoi Ujjal,
Phukan Ashwini K.
Publication year - 2013
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.24485
Subject(s) - reactivity (psychology) , electrophile , nucleophile , chemistry , lone pair , dissociation (chemistry) , computational chemistry , carbon fibers , carbon atom , bond dissociation energy , proton affinity , organic chemistry , molecule , ring (chemistry) , catalysis , materials science , medicine , alternative medicine , pathology , composite number , composite material , ion , protonation
Quantum chemical calculations are performed on different carbon bases to understand the origin of their reactivity. Both carbon(0) and carbon(II) bases may show very high values of second proton affinity as well as bond dissociation energies for gem‐dimetallation. Thus, their distinction becomes blurred when subjected to electrophilic attack. However, unlike carbon(0) bases, carbon(II) bases are ambiphilic in nature owing to the presence of a σ symmetric lone pair and a vacant π orbital concentrated on the central carbon atom. Thus, they may show different reactivity when subjected to nucleophilic attack. This reactivity difference may be considered as another distinction between these two classes of compounds. © 2013 Wiley Periodicals, Inc.