Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives

Theoretical and experimental studies on 3J C2H6eq NMR spin - spin coupling constants in both the 2-X-4-t-butyl-cyclohexanone (X = H, CH 3, F, Cl, and Br) and in their alcohol derivatives series are reported. Results thus found are rationalized in terms of the transmission of the Fermi contact contri...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Favaro, D.C., Ducati, L.C., Dos Santos, F.P., Contreras, R.H., Tormena, C.F.
Formato: JOUR
Materias:
Alcohol derivatives
Coupling constants
Experimental studies
Fermi contact
Halogen atoms
Lone pair
Spin coupling constants
Strong interaction
Bromine
Chlorine
Couplings
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_10895639_v115_n50_p14539_Favaro
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_10895639_v115_n50_p14539_Favaro
record_format dspace
spelling todo:paper_10895639_v115_n50_p14539_Favaro2023-10-03T16:04:44Z Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives Favaro, D.C. Ducati, L.C. Dos Santos, F.P. Contreras, R.H. Tormena, C.F. Alcohol derivatives Coupling constants Experimental studies Fermi contact Halogen atoms Lone pair Spin coupling constants Strong interaction Bromine Chlorine Couplings Theoretical and experimental studies on 3J C2H6eq NMR spin - spin coupling constants in both the 2-X-4-t-butyl-cyclohexanone (X = H, CH 3, F, Cl, and Br) and in their alcohol derivatives series are reported. Results thus found are rationalized in terms of the transmission of the Fermi contact contribution to such couplings. To this end, dependencies of 3J C2H6eq couplings versus the C 2 - C 1 - C 6 angle are compared in both series for equatorial and axial X orientations. The main trend is described in terms of the rear lobes interaction. Besides, for X = halogen atom in equatorial orientation a rather strong interaction between oxygen and halogen lone pairs is observed, and its influence on 3J C2H6eq couplings is discussed and rationalized in terms of different Fermi contact transmission pathways. (Figure presented) © 2011 American Chemical Society. Fil:Contreras, R.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_10895639_v115_n50_p14539_Favaro
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Alcohol derivatives
Coupling constants
Experimental studies
Fermi contact
Halogen atoms
Lone pair
Spin coupling constants
Strong interaction
Bromine
Chlorine
Couplings
spellingShingle Alcohol derivatives
Coupling constants
Experimental studies
Fermi contact
Halogen atoms
Lone pair
Spin coupling constants
Strong interaction
Bromine
Chlorine
Couplings
Favaro, D.C.
Ducati, L.C.
Dos Santos, F.P.
Contreras, R.H.
Tormena, C.F.
Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
topic_facet Alcohol derivatives
Coupling constants
Experimental studies
Fermi contact
Halogen atoms
Lone pair
Spin coupling constants
Strong interaction
Bromine
Chlorine
Couplings
description Theoretical and experimental studies on 3J C2H6eq NMR spin - spin coupling constants in both the 2-X-4-t-butyl-cyclohexanone (X = H, CH 3, F, Cl, and Br) and in their alcohol derivatives series are reported. Results thus found are rationalized in terms of the transmission of the Fermi contact contribution to such couplings. To this end, dependencies of 3J C2H6eq couplings versus the C 2 - C 1 - C 6 angle are compared in both series for equatorial and axial X orientations. The main trend is described in terms of the rear lobes interaction. Besides, for X = halogen atom in equatorial orientation a rather strong interaction between oxygen and halogen lone pairs is observed, and its influence on 3J C2H6eq couplings is discussed and rationalized in terms of different Fermi contact transmission pathways. (Figure presented) © 2011 American Chemical Society.
format JOUR
author Favaro, D.C.
Ducati, L.C.
Dos Santos, F.P.
Contreras, R.H.
Tormena, C.F.
author_facet Favaro, D.C.
Ducati, L.C.
Dos Santos, F.P.
Contreras, R.H.
Tormena, C.F.
author_sort Favaro, D.C.
title Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
title_short Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
title_full Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
title_fullStr Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
title_full_unstemmed Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
title_sort stereochemical dependence of 3j ch coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
url http://hdl.handle.net/20.500.12110/paper_10895639_v115_n50_p14539_Favaro
work_keys_str_mv AT favarodc stereochemicaldependenceof3jchcouplingconstantsin2substituted4tbutylcyclohexanoneandtheiralcoholderivatives
AT ducatilc stereochemicaldependenceof3jchcouplingconstantsin2substituted4tbutylcyclohexanoneandtheiralcoholderivatives
AT dossantosfp stereochemicaldependenceof3jchcouplingconstantsin2substituted4tbutylcyclohexanoneandtheiralcoholderivatives
AT contrerasrh stereochemicaldependenceof3jchcouplingconstantsin2substituted4tbutylcyclohexanoneandtheiralcoholderivatives
AT tormenacf stereochemicaldependenceof3jchcouplingconstantsin2substituted4tbutylcyclohexanoneandtheiralcoholderivatives
_version_ 1782025228708216832

Ejemplares similares