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Theoretical investigation of the substituent effects in the conformational isomerism of bromoalkoxycyclohexanes.
- Source :
- Computational & Theoretical Chemistry; Nov2012, Vol. 999, p89-92, 4p
- Publication Year :
- 2012
-
Abstract
- Abstract: Isodesmic reactions and the energy of intramolecular interactions in bromoalkoxycyclohexanes (alkoxy=OMe, OEt, O <superscript>i</superscript> Pr and O <superscript>t</superscript> Bu) 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. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 2210271X
- Volume :
- 999
- Database :
- Supplemental Index
- Journal :
- Computational & Theoretical Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 83326316
- Full Text :
- https://doi.org/10.1016/j.comptc.2012.08.019