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Type: Artigo de periódico
Title: Theoretical and infrared studies on the conformations of monofluorophenols
Author: Moreira, MA
Cormanich, RA
de Rezende, FMP
Silla, JM
Tormena, CF
Rittner, R
Ramalho, TC
Freitas, MP
Abstract: Theoretical calculations for the isolated state indicate the presence of two conformers (A and B) for 2- and 3-fluorophenols, while a single form exists for 4-fluorophenol, as it is well known. The conformer with the hydroxyl hydrogen directed toward the fluorine atom (A) in 2-fluorophenol is calculated to be significantly more stable than the second form, while similar behavior is not obtained for the meta isomer. The infrared C-F stretching intensities confirm these findings in cyclohexane solution, where internal hydrogen bonding in 2-fluorophenol is supposed to be a stabilizing effect of A, but the figure changes in acetonitrile solution and neat liquid, where the most polar conformer B is preferred and intermolecular hydrogen bonding seems to take place, as confirmed by the broadening and shifting of the O-H stretching band. In fact, the strong solvent effect in 2-fluorophenol suggests that conformer A is the most stable form in the isolated state and nonpolar solution predominantly due to dipolar repulsion in B. (C) 2011 Elsevier B.V. All rights reserved.
Subject: Fluorophenols
Conformational analysis
Infrared intensities
Solvent effect
Country: Holanda
Editor: Elsevier Science Bv
Rights: fechado
Identifier DOI: 10.1016/j.molstruc.2011.05.012
Date Issue: 2012
Appears in Collections:Unicamp - Artigos e Outros Documentos

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