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An n→π* interaction reduces the electrophilicity of the acceptor carbonyl group.

Carbonyl-carbonyl (C&z.dbd; O...C'&z.dbd; 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 ( pi *) of an acceptor carbonyl group. Analyses of high-resolution protein s... Full description

Journal Title: Chemical communications (Cambridge England), September 25, 2013, Vol.49(74), pp.8166-8168
Main Author: Choudhary, Amit
Other Authors: Fry, Charles G , Kamer, Kimberli J , Raines, Ronald T
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1364-548X ; DOI: 1364-548X ; DOI: 10.1039/c3cc44573a
Link: http://search.proquest.com/docview/1426751139/?pq-origsite=primo
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title: An n→π* interaction reduces the electrophilicity of the acceptor carbonyl group.
format: Article
creator:
  • Choudhary, Amit
  • Fry, Charles G
  • Kamer, Kimberli J
  • Raines, Ronald T
subjects:
  • Electrons–Chemistry
  • Esters–Chemistry
  • Imidazolidines–Chemistry
  • Models, Molecular–Chemistry
  • Molecular Structure–Chemistry
  • Oxidation-Reduction–Chemistry
  • Esters
  • Imidazolidines
ispartof: Chemical communications (Cambridge, England), September 25, 2013, Vol.49(74), pp.8166-8168
description: Carbonyl-carbonyl (C&z.dbd; O...C'&z.dbd; 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 ( pi *) of an acceptor carbonyl group. Analyses of high-resolution protein structures suggest that these carbonyl-carbonyl interactions prefer to occur in pairs, that is, one donor per acceptor. Here, the reluctance of the acceptor carbonyl group (C'&z.dbd; O') to engage in more than one n arrow right pi * 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 n arrow right pi * electron delocalization. This diminished electrophilicity discourages a second n arrow right pi * interaction with the acceptor carbonyl group.
language: eng
source:
identifier: E-ISSN: 1364-548X ; DOI: 1364-548X ; DOI: 10.1039/c3cc44573a
fulltext: fulltext
issn:
  • 1364548X
  • 1364-548X
url: Link


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titleAn n→π* interaction reduces the electrophilicity of the acceptor carbonyl group.
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ispartofChemical communications (Cambridge, England), September 25, 2013, Vol.49(74), pp.8166-8168
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subjectElectrons–Chemistry ; Esters–Chemistry ; Imidazolidines–Chemistry ; Models, Molecular–Chemistry ; Molecular Structure–Chemistry ; Oxidation-Reduction–Chemistry ; Esters ; Imidazolidines
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descriptionCarbonyl-carbonyl (C&z.dbd; O...C'&z.dbd; 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 ( pi *) of an acceptor carbonyl group. Analyses of high-resolution protein structures suggest that these carbonyl-carbonyl interactions prefer to occur in pairs, that is, one donor per acceptor. Here, the reluctance of the acceptor carbonyl group (C'&z.dbd; O') to engage in more than one n arrow right pi * 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 n arrow right pi * electron delocalization. This diminished electrophilicity discourages a second n arrow right pi * interaction with the acceptor carbonyl group.
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