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Type: Artigo de periódico
Title: A H-1 NMR and molecular modelling investigation of diastereotopic methylene hydrogen atoms
Author: Tormena, CF
Freitas, MP
Rittner, R
Abraham, RJ
Abstract: The H-1 NMR spectra of methyl 3-bromo-2-methylpropionate (1a) and the corresponding chloro compound (2a) show no long-range coupling between the methyl and methylene protons. In contrast, in the analogous dihalocompounds, methyl 2,3-dibromo-2-methylpropionate (1b) and methyl 2,3-dichloro2-methylpropionate (2b), one of the methylene protons exhibits a large (4)J(HH) coupling (0.8 Hz) to the methyl group, but the other proton shows no observable splitting. This can be explained quantitatively by calculations of the conformational preferences in these compounds combined with the known orientation dependence of the (4)J(HH)couplings. One conformer predominates in the dihalo compounds 1b and 2b, and this is responsible for the (4)J(HH) coupling. In la and 2a all three conformers are populated and the (4)J(HH) couplings average to zero. The technique is a potentially general method of unambiguously assigning diastereotopic methylene protons. Copyright (C) 2002 John Wiley Sons, Ltd.
Subject: H-1 NMR spectroscopy
molecular modelling
diastereotopic hydrogen
Country: Inglaterra
Editor: John Wiley & Sons Ltd
Rights: fechado
Identifier DOI: 10.1002/mrc.1011
Date Issue: 2002
Appears in Collections:Unicamp - Artigos e Outros Documentos

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