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Type: Artigo de periódico
Title: Solvent effects in the conformational stability of alpha-substituted acetamides through theoretical and experimental data
Author: Pedersoli, S
Tormena, CF
Rittner, R
Abstract: The conformational stability of fluoroacetamide (1), chloroacetamide (2), cyanoacetamide (3) and bromoacetamide (4) was studied using theoretical calculations in vapor phase and taking into account solvent effects. The conformational preference was determined by theoretical and experimental coupling constant values ((2)J(CH) and (3)J(CH)). Theoretical results, including the solvent effects by PCM, allowed the characterization of the most stable conformers present in the studied solutions: trans rotamer for compounds 1 and 2, cis rotamer for compound 3 and gauche and trans rotamers for compound 4. The conformational preferences were explained by electrostatic and dipole-dipole interactions, steric effects and by the hyperconjugative interactions, which were revealed by NBO data. (c) 2007 Elsevier B.V. All rights reserved.
Subject: conformational stability
solvent effects
x-substituted acetatnidcs
NBO analysis
Country: Holanda
Editor: Elsevier Science Bv
Rights: fechado
Identifier DOI: 10.1016/j.molstruc.2007.04.037
Date Issue: 2008
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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