Two of the stereoisomers of the title compound were prepared and their dipole moments were measured. For the r-1,c-3-dichloro-t-5-methylcyclohexane, the free energy difference between conformers with axial-axial (aa) and equatorial-equatorial (ee) chlorines was measured by a variable temperature NMR method, and the value found was 1.3 ± 0.2 Kcal/mol-1 (in acetone) favoring the latter. Molecular mechanics studies show that the solvation energy and the electrostatics are of major importance in understanding this equilibrium. Calculations show the effect of the methyl group is essentially additive, and give for cis-1,3-dichlorocyclohexane itself ee{measured angle}aa DH+ 3.0 kcal mol-1 (acetone).
TY - JOUR
AU - Došen-Mićović, Ljiljana
AU - Jeremić, Dragoslav
AU - Allinger, Norman L.
PY - 1981
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4423
AB - Two of the stereoisomers of the title compound were prepared and their dipole moments were measured. For the r-1,c-3-dichloro-t-5-methylcyclohexane, the free energy difference between conformers with axial-axial (aa) and equatorial-equatorial (ee) chlorines was measured by a variable temperature NMR method, and the value found was 1.3 ± 0.2 Kcal/mol-1 (in acetone) favoring the latter. Molecular mechanics studies show that the solvation energy and the electrostatics are of major importance in understanding this equilibrium. Calculations show the effect of the methyl group is essentially additive, and give for cis-1,3-dichlorocyclohexane itself ee{measured angle}aa DH+ 3.0 kcal mol-1 (acetone).
PB - Elsevier
T2 - Tetrahedron
T1 - The conformational equilibrium of 1,3-dichloro-5-methylcyclohexane
VL - 37
IS - 20
SP - 3455
EP - 3461
DO - 10.1016/S0040-4020(01)98859-3
ER -
@article{
author = "Došen-Mićović, Ljiljana and Jeremić, Dragoslav and Allinger, Norman L.",
year = "1981",
abstract = "Two of the stereoisomers of the title compound were prepared and their dipole moments were measured. For the r-1,c-3-dichloro-t-5-methylcyclohexane, the free energy difference between conformers with axial-axial (aa) and equatorial-equatorial (ee) chlorines was measured by a variable temperature NMR method, and the value found was 1.3 ± 0.2 Kcal/mol-1 (in acetone) favoring the latter. Molecular mechanics studies show that the solvation energy and the electrostatics are of major importance in understanding this equilibrium. Calculations show the effect of the methyl group is essentially additive, and give for cis-1,3-dichlorocyclohexane itself ee{measured angle}aa DH+ 3.0 kcal mol-1 (acetone).",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "The conformational equilibrium of 1,3-dichloro-5-methylcyclohexane",
volume = "37",
number = "20",
pages = "3455-3461",
doi = "10.1016/S0040-4020(01)98859-3"
}
Došen-Mićović, L., Jeremić, D.,& Allinger, N. L.. (1981). The conformational equilibrium of 1,3-dichloro-5-methylcyclohexane. in Tetrahedron
Elsevier., 37(20), 3455-3461.
https://doi.org/10.1016/S0040-4020(01)98859-3
Došen-Mićović L, Jeremić D, Allinger NL. The conformational equilibrium of 1,3-dichloro-5-methylcyclohexane. in Tetrahedron. 1981;37(20):3455-3461.
doi:10.1016/S0040-4020(01)98859-3 .
Došen-Mićović, Ljiljana, Jeremić, Dragoslav, Allinger, Norman L., "The conformational equilibrium of 1,3-dichloro-5-methylcyclohexane" in Tetrahedron, 37, no. 20 (1981):3455-3461,
https://doi.org/10.1016/S0040-4020(01)98859-3 . .
