Revisiting the reactivity of different carbon bases: A theoretical study
Article first published online: 11 JUN 2013
Copyright © 2013 Wiley Periodicals, Inc.
International Journal of Quantum Chemistry
Volume 113, Issue 22, pages 2471–2477, 15 November 2013
How to Cite
How to cite this article: Int. J. Quantum Chem. 2013, 113, 2471–2477. DOI: 10.1002/qua.24485, , .
- Issue published online: 7 OCT 2013
- Article first published online: 11 JUN 2013
- Manuscript Accepted: 10 MAY 2013
- Manuscript Revised: 5 APR 2013
- Manuscript Received: 25 JAN 2013
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.