Unexpected chirality in trans-1,4-dicyanocyclohexane
The experimental non-zero dipole moment of trans-1,4-dicyanocyclohexane was verified through a procedure little sensitive to solute/solvent interactions. This value cannot be explained on the basis of the generally accepted centrosymmetry for trans-1,4-derivatives of cyclohexane. NMR data of both th...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00222860_v172_nC_p355_Baron |
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todo:paper_00222860_v172_nC_p355_Baron2023-10-03T14:30:34Z Unexpected chirality in trans-1,4-dicyanocyclohexane Barón, M. Medrano, J.A. Ferraro, M. Buep, A.H. The experimental non-zero dipole moment of trans-1,4-dicyanocyclohexane was verified through a procedure little sensitive to solute/solvent interactions. This value cannot be explained on the basis of the generally accepted centrosymmetry for trans-1,4-derivatives of cyclohexane. NMR data of both this compound and its C-1, C-4 di-deuteroderivative, as well as semi-empirical theoretical calculations with the MNDO methods show that besides a centro-symmetric form there are also low energy stable non-centrosymmetric geometries. The latter exist as a helical deformation that can account for the non-zero value of the experimental dipole moment. © 1988. Fil:Barón, M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Medrano, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ferraro, M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Buep, A.H. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00222860_v172_nC_p355_Baron |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| description |
The experimental non-zero dipole moment of trans-1,4-dicyanocyclohexane was verified through a procedure little sensitive to solute/solvent interactions. This value cannot be explained on the basis of the generally accepted centrosymmetry for trans-1,4-derivatives of cyclohexane. NMR data of both this compound and its C-1, C-4 di-deuteroderivative, as well as semi-empirical theoretical calculations with the MNDO methods show that besides a centro-symmetric form there are also low energy stable non-centrosymmetric geometries. The latter exist as a helical deformation that can account for the non-zero value of the experimental dipole moment. © 1988. |
| format |
JOUR |
| author |
Barón, M. Medrano, J.A. Ferraro, M. Buep, A.H. |
| spellingShingle |
Barón, M. Medrano, J.A. Ferraro, M. Buep, A.H. Unexpected chirality in trans-1,4-dicyanocyclohexane |
| author_facet |
Barón, M. Medrano, J.A. Ferraro, M. Buep, A.H. |
| author_sort |
Barón, M. |
| title |
Unexpected chirality in trans-1,4-dicyanocyclohexane |
| title_short |
Unexpected chirality in trans-1,4-dicyanocyclohexane |
| title_full |
Unexpected chirality in trans-1,4-dicyanocyclohexane |
| title_fullStr |
Unexpected chirality in trans-1,4-dicyanocyclohexane |
| title_full_unstemmed |
Unexpected chirality in trans-1,4-dicyanocyclohexane |
| title_sort |
unexpected chirality in trans-1,4-dicyanocyclohexane |
| url |
http://hdl.handle.net/20.500.12110/paper_00222860_v172_nC_p355_Baron |
| work_keys_str_mv |
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| _version_ |
1782023918996946944 |