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Issue 74, 2013
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An nπ* interaction reduces the electrophilicity of the acceptor carbonyl group

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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

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Publication details

The article was received on 18 Jun 2013, accepted on 12 Jul 2013 and first published on 16 Jul 2013


Article type: Communication
DOI: 10.1039/C3CC44573A
Citation: Chem. Commun., 2013,49, 8166-8168
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    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

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