Please use this identifier to cite or link to this item: http://repositorio.ufla.br/jspui/handle/1/41570
Title: Theoretical investigation of the substituent effects in the conformational isomerism of bromoalkoxycyclohexanes
Keywords: Conformational analysis
Isodesmic reactions
Intramolecular interactions
Bromoalkoxycyclohexanes
Issue Date: 1-Nov-2012
Publisher: Elsevier
Citation: SILLA, J. M.; FREITAS, M. P. Theoretical investigation of the substituent effects in the conformational isomerism of bromoalkoxycyclohexanes. Computational and Theoretical Chemistry, [S.l.], v. 999, p. 89-92, Nov. 2012. DOI: 10.1016/j.comptc.2012.08.019.
Abstract: Isodesmic reactions and the energy of intramolecular interactions in bromoalkoxycyclohexanes (alkoxy = OMe, OEt, OiPr and OtBu) were computed to evaluate the effect of bromine and alkoxy groups when bonded together in a cyclohexane ring to give cis and trans-1,2, 1,3 and 1,4 isomers. According to the enthalpy energies obtained from the isodesmic reactions, the bromine atom is preferred to be introduced axially in methoxycyclohexane to give trans-1-bromo-2-methoxycyclohexane; otherwise, equatorial introduction of the bromine atom is favoured. Either direct or indirect intramolecular interactions involving OR and Br, obtained from comparison with the conformational energies of the monosubstituted cyclohexanes, indicate a preference for bromine axially oriented, except for the cis-1,3 isomer, in which the OR and Br groups experience high steric hindrance to each other. The effect of R is generally invariant.
URI: https://www.sciencedirect.com/science/article/abs/pii/S2210271X12004148
http://repositorio.ufla.br/jspui/handle/1/41570
Appears in Collections:DQI - Artigos publicados em periódicos

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