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Type: Artigo de periódico
Title: Conformational. preferences for N,N-dimethyl-2-haloacetamides (halo= F, Cl, Br and I) through theoretical and experimental studies: An unexpected orbital interaction
Author: Martins, CR
Rittner, R
Tormena, CF
Abstract: Conformational preferences and orbital interactions of N,N-dimethyl-2-fluoroacetamide (1), N,N-dimethyl-2-chloroacetamide (2), N,Ndimethyl-2-bromoacetamide (3) and N,N-dimethyl-2-iodoacetamide (4) were analyzed using experimental infra-red data, theoretical calculations and NBO analysis. The conformational equilibria of compounds 1-4 can be represented by their cis and gauche rotamers. The gauche form of I is stable in the vapor phase and in a non-polar solvent, but the cis is predominant in a polar solvent. For 2-4 the gauche form is more stable than the cis, in both the vapor and liquid phases. These conformational preferences were attributed to the orbital interaction between two antibonding orbitals, pi*(C=O)->sigma*(C-X). This unexpected interaction was possibly due to the high (0.3) electron density on pi*C=O, which results from the interaction between one nitrogen lone pair and pi*C -> O. (c) 2005 Elsevier B.V. All rights reserved.
Subject: conformational analysis
theoretical calculations
infra-red spectroscopy
Country: Holanda
Editor: Elsevier Science Bv
Rights: fechado
Identifier DOI: 10.1016/j.theochem.2005.04.033
Date Issue: 2005
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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