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Type: Artigo de periódico
Title: On the stereoelectronic effects governing the rotational isomerism of 1,2-di-haloethanes
Author: Souza, FR
Freitas, MP
Rittner, R
Abstract: The rotational isomerism of 1,2-di-haloethanes. namely 1,2-difluoro- (1), 1,2-dicliloro- (2), 1,2-dibromo(3) and 1,2-diiodo-ethane (4). was theoretically evaluated in this Work. Our DFT calculations showed that the gauche conformer is prevalent in 1, whilst the trans form is largely favoured in the remaining compounds, at the isolated state. NBO analyses revealed that the fluorinated compound experiences the gauche effect, which is due to a C-H/C-F hyperconjugation. Classical steric/electrostatic repulsion and hyperconjugative interactions are more competitive in 2, and the C-X/C-X-center dot electron delocalization (X = Br and I) strongly favours the trans conformer in 3 and 4. (C) 2008 Elsevier B.V. All rights reserved.
Subject: conformational analysis
classical effects
Country: Holanda
Editor: Elsevier Science Bv
Citation: Journal Of Molecular Structure-theochem. Elsevier Science Bv, v. 863, n. 41699, n. 137, n. 140, 2008.
Rights: fechado
Identifier DOI: 10.1016/j.theochem.2008.06.003
Date Issue: 2008
Appears in Collections:Unicamp - Artigos e Outros Documentos

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