Jump to main content
Jump to site search

Issue 74, 2013
Previous Article Next Article

An nπ* interaction reduces the electrophilicity of the acceptor carbonyl group

Author affiliations

Abstract

Carbonylcarbonyl (C[double bond, length as m-dash]O⋯C′[double bond, length as m-dash]O′) interactions are ubiquitous in both small and large molecular systems. This interaction involves delocalization of a lone pair (n) of a donor oxygen into the antibonding orbital (π*) of an acceptor carbonyl group. Analyses of high-resolution protein structures suggest that these carbonylcarbonyl interactions prefer to occur in pairs, that is, one donor per acceptor. Here, the reluctance of the acceptor carbonyl group (C′[double bond, length as m-dash]O′) to engage in more than one nπ* electron delocalization is probed using imidazolidine-based model systems with one acceptor carbonyl group and two equivalent donor carbonyl groups. The data indicate that the electrophilicity of the acceptor carbonyl group is reduced when it engages in nπ* electron delocalization. This diminished electrophilicity discourages a second nπ* interaction with the acceptor carbonyl group.

Graphical abstract: An n→π* interaction reduces the electrophilicity of the acceptor carbonyl group

Back to tab navigation

Supplementary files

Article information


Submitted
18 Jun 2013
Accepted
12 Jul 2013
First published
16 Jul 2013

Chem. Commun., 2013,49, 8166-8168
Article type
Communication

An nπ* interaction reduces the electrophilicity of the acceptor carbonyl group

A. Choudhary, C. G. Fry, K. J. Kamer and R. T. Raines, Chem. Commun., 2013, 49, 8166
DOI: 10.1039/C3CC44573A

Social activity

Search articles by author

Spotlight

Advertisements