Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/202259
Type: Artigo de periódico
Title: The Conformational Analysis Of 2-halocyclooctanones.
Author: Rozada, Thiago C
Gauze, Gisele F
Rosa, Fernanda A
Favaro, Denize C
Rittner, Roberto
Pontes, Rodrigo M
Basso, Ernani A
Abstract: The establishment of the most stable structures of eight membered rings is a challenging task to the field of conformational analysis. In this work, a series of 2-halocyclooctanones were synthesized (including fluorine, chlorine, bromine and iodine derivatives) and submitted to conformational studies using a combination of theoretical calculation and infrared spectroscopy. For each compound, four conformations were identified as the most important ones. These conformations are derived from the chair-boat conformation of cyclooctanone. The pseudo-equatorial (with respect to the halogen) conformer is preferred in vacuum and in low polarity solvents for chlorine, bromine and iodine derivatives. For 2-fluorocyclooctanone, the preferred conformation in vacuum is pseudo-axial. In acetonitrile, the pseudo-axial conformer becomes the most stable for the chlorine derivative. According to NBO calculations, the conformational preference is not dictated by electron delocalization, but by classical electrostatic repulsions.
Subject: Conformations
Halocyclooctanones
Infrared
Theoretical Calculations
Rights: fechado
Identifier DOI: 10.1016/j.saa.2014.08.052
Address: http://www.ncbi.nlm.nih.gov/pubmed/25218227
Date Issue: 2015
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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