Unexpected chirality in trans-1,4-dicyanocyclohexane

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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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Detalles Bibliográficos
Autores principales: Barón, Máximo, Medrano, Jorge A., Ferraro, Marta Beatriz, Buep, Adrián Hugo
Publicado: 1988
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v172_nC_p355_Baron
http://hdl.handle.net/20.500.12110/paper_00222860_v172_nC_p355_Baron
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_00222860_v172_nC_p355_Baron
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spelling paper:paper_00222860_v172_nC_p355_Baron2023-06-08T14:48:52Z Unexpected chirality in trans-1,4-dicyanocyclohexane Barón, Máximo Medrano, Jorge A. Ferraro, Marta Beatriz Buep, Adrián Hugo 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. 1988 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v172_nC_p355_Baron 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.
author Barón, Máximo
Medrano, Jorge A.
Ferraro, Marta Beatriz
Buep, Adrián Hugo
spellingShingle Barón, Máximo
Medrano, Jorge A.
Ferraro, Marta Beatriz
Buep, Adrián Hugo
Unexpected chirality in trans-1,4-dicyanocyclohexane
author_facet Barón, Máximo
Medrano, Jorge A.
Ferraro, Marta Beatriz
Buep, Adrián Hugo
author_sort Barón, Máximo
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
publishDate 1988
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v172_nC_p355_Baron
http://hdl.handle.net/20.500.12110/paper_00222860_v172_nC_p355_Baron
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AT medranojorgea unexpectedchiralityintrans14dicyanocyclohexane
AT ferraromartabeatriz unexpectedchiralityintrans14dicyanocyclohexane
AT buepadrianhugo unexpectedchiralityintrans14dicyanocyclohexane
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