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Type: Artigo
Title: The Role Of Nonbonding Interactions And The Presence Of Fluoride On The Conformational Isomerism Of 1,2-ethanediol
Author: Silva
Weslley G. D. P.; Silla
Josue M.; Cormanich
Rodrigo A.; Fernandes
Sergio A.; Freitas
Matheus P.
Abstract: This work reports the analysis of the effects ruling the conformational preference of 1,2-ethanediol (1,2-ED) using theoretical calculations, since there is no general consensus about the role of intramolecular hydrogen bond on the conformational isomerism of 1,2-ED. While the predominance of the gauche conformers along with the O-C-C-O fragment relative to the trans ones was found to be mainly due to hyperconjugation, the orientation of the hydroxyl groups is better described by a balance between low steric hindrance and high stabilization from hyperconjugation than by intramolecular hydrogen bond. Nevertheless, the presence of a fluoride anion induces a conformational change in 1,2-ED that maximizes hydrogen bonds between the fluoride and the hydroxyl groups. This effect was observed experimentally by the shift of H-1(O) and F-19 NMR signals upon complexation, then suggesting that compounds containing the 1,2-ED moiety can be possible anion transporters. (C) 2016 Elsevier B.V. All rights reserved.
Subject: 1,2-ethanediol
Conformational Analysis
Hydrogen Bond
Editor: Elsevier Science BV
Rights: fechado
Identifier DOI: 10.1016/j.chemphys.2016.04.018
Date Issue: 2016
Appears in Collections:Unicamp - Artigos e Outros Documentos

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