Orbital interactions in 2-Halocyclohexanones as analyzed by means of theoretical calculations

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Título:	Orbital interactions in 2-Halocyclohexanones as analyzed by means of theoretical calculations
Palavras-chave:	Isodesmic reaction Conformational analysis NBO 2-Halocyclohexanones Natural bond orbital (NBO)
Data do documento:	Fev-2010
Editor:	Elsevier
Citação:	COELHO, J. V.; FREITAS, M. P. Orbital interactions in 2-Halocyclohexanones as analyzed by means of theoretical calculations. Journal of Molecular Structure: THEOCHEM, [S.l.], v. 941, n. 1-3, p. 53-55, Feb. 2010. DOI: 10.1016/j.theochem.2009.10.039.
Resumo:	The stereoelectronic interactions governing the conformational isomerism of 2-halocyclohexanones have been investigated by using an isodesmic reaction model. It has been found that 2-axial halogenation of cyclohexanone is thermodynamically favoured, whilst insertion of an equatorial bromine or iodine is not. Overall, inclusion of axial halogens in cyclohexanone is preferred to equatorial entrance and, according to NBO calculations, this behaviour is due to electron donation from nonbonding and C-X orbitals to πCO∗ antibonding orbital, in addition to steric and electrostatic effects.
URI:	https://www.sciencedirect.com/science/article/abs/pii/S0166128009007398 http://repositorio.ufla.br/jspui/handle/1/41802
Aparece nas coleções:	DQI - Artigos publicados em periódicos

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