Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/61926
Type: Artigo de periódico
Title: NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. (3)J(CH) couplings in alpha-substituted acetamides
Author: Pedersoli, S
dos Santos, FP
Rittner, R
Contreras, RH
Tormena, CF
Abstract: in this work (3)JcH spin-spin coupling constants (SSCCs) for the cis- and trans-conformers for alpha-X-acetamides (X = F, Cl, Bir and CN) (1-4) were studied in detail since they were found to be notably different for both conformers. These differences are rationalized as originating in the changes of the strong negative hyperconjugative interactions that take place within the carbonyl group. Such changes are found to depend not only on conformation, but also on solvent. For the cis-conformers there is a close proximity between the X-substituent and the in-plane oxygen lone pair of pure p character, which affects notably their respective negative hyperconjugative interactions. Both the efficiency for transmitting the Fermi contact (FC) term through the coupling pathway of (3)(jCH) SSCCs and its potential as a probe to study the stereochemical properties of the XH2C group are discussed. Copyright (c) 2008 John Wiley & Sons, Ltd.
Subject: FC transmission
(3)J(CH) couplings
negative hyperconjugative interactions
Country: Inglaterra
Editor: John Wiley & Sons Ltd
Rights: fechado
Identifier DOI: 10.1002/mrc.2158
Date Issue: 2008
Appears in Collections:Unicamp - Artigos e Outros Documentos

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