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Type: Artigo de periódico
Title: The Conformational Analysis Of 2-halocyclooctanones
Author: Rozada T.C.
Gauze G.F.
Rosa F.A.
Favaro D.C.
Rittner R.
Pontes R.M.
Basso E.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.
Editor: Elsevier
Rights: fechado
Identifier DOI: 10.1016/j.saa.2014.08.052
Date Issue: 2015
Appears in Collections:Unicamp - Artigos e Outros Documentos

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