Intramolecular electric field effect on a 1J(C,H) NMR spin-spin coupling constant. An experimental and theoretical study

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An experimental study of the effects of intramolecular electric fields on 1J(C,H) coupling constants involving a formyl proton in a series of 5-X-salicylaldehydes is reported. The particularly large electric field component along the Cc-Hf bond, calculated for X = NO2, leads to a measured substituen...

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Autores principales: De Kowalewski, D.G., Kowalewski, V.J., Peralta, J.E., Eskuche, G., Contreras, R.H., Esteban, A.L., Galache, M.P., Díez, E.
Formato: JOUR
Materias:
5-X-salicylaldehydes
13C NMR
1J(C,H)
Intramolecular electric field
NMR
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_07491581_v37_n3_p227_DeKowalewski
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_07491581_v37_n3_p227_DeKowalewski
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spelling todo:paper_07491581_v37_n3_p227_DeKowalewski2023-10-03T15:39:26Z Intramolecular electric field effect on a 1J(C,H) NMR spin-spin coupling constant. An experimental and theoretical study De Kowalewski, D.G. Kowalewski, V.J. Peralta, J.E. Eskuche, G. Contreras, R.H. Esteban, A.L. Galache, M.P. Díez, E. 5-X-salicylaldehydes 13C NMR 1J(C,H) Intramolecular electric field NMR An experimental study of the effects of intramolecular electric fields on 1J(C,H) coupling constants involving a formyl proton in a series of 5-X-salicylaldehydes is reported. The particularly large electric field component along the Cc-Hf bond, calculated for X = NO2, leads to a measured substituent effect of 7.36 Hz. For other X substituents a linear correlation was found between the calculated substituent electric field component along the Cc-Hf bond and the substituent effect on 1J(Cc,Hf). To determine if 5-X substituents affect the intramolecular C=O⋯H-O hydrogen bond, NBO analyses were carried out on 5-NO2- and 5-H-salicylaldehyde, and they were compared with those corresponding to benzaldehyde and phenol. The effects of interactions other than the electrostatic one on 1J(Cc,Hf) couplings were ruled out. The experimental results are in agreement with theoretical predictions published previously. Copyright © 1999 John Wiley & Sons, Ltd. Fil:Kowalewski, V.J. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Peralta, J.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Eskuche, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 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_07491581_v37_n3_p227_DeKowalewski
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic 5-X-salicylaldehydes
13C NMR
1J(C,H)
Intramolecular electric field
NMR
spellingShingle 5-X-salicylaldehydes
13C NMR
1J(C,H)
Intramolecular electric field
NMR
De Kowalewski, D.G.
Kowalewski, V.J.
Peralta, J.E.
Eskuche, G.
Contreras, R.H.
Esteban, A.L.
Galache, M.P.
Díez, E.
Intramolecular electric field effect on a 1J(C,H) NMR spin-spin coupling constant. An experimental and theoretical study
topic_facet 5-X-salicylaldehydes
13C NMR
1J(C,H)
Intramolecular electric field
NMR
description An experimental study of the effects of intramolecular electric fields on 1J(C,H) coupling constants involving a formyl proton in a series of 5-X-salicylaldehydes is reported. The particularly large electric field component along the Cc-Hf bond, calculated for X = NO2, leads to a measured substituent effect of 7.36 Hz. For other X substituents a linear correlation was found between the calculated substituent electric field component along the Cc-Hf bond and the substituent effect on 1J(Cc,Hf). To determine if 5-X substituents affect the intramolecular C=O⋯H-O hydrogen bond, NBO analyses were carried out on 5-NO2- and 5-H-salicylaldehyde, and they were compared with those corresponding to benzaldehyde and phenol. The effects of interactions other than the electrostatic one on 1J(Cc,Hf) couplings were ruled out. The experimental results are in agreement with theoretical predictions published previously. Copyright © 1999 John Wiley & Sons, Ltd.
format JOUR
author De Kowalewski, D.G.
Kowalewski, V.J.
Peralta, J.E.
Eskuche, G.
Contreras, R.H.
Esteban, A.L.
Galache, M.P.
Díez, E.
author_facet De Kowalewski, D.G.
Kowalewski, V.J.
Peralta, J.E.
Eskuche, G.
Contreras, R.H.
Esteban, A.L.
Galache, M.P.
Díez, E.
author_sort De Kowalewski, D.G.
title Intramolecular electric field effect on a 1J(C,H) NMR spin-spin coupling constant. An experimental and theoretical study
title_short Intramolecular electric field effect on a 1J(C,H) NMR spin-spin coupling constant. An experimental and theoretical study
title_full Intramolecular electric field effect on a 1J(C,H) NMR spin-spin coupling constant. An experimental and theoretical study
title_fullStr Intramolecular electric field effect on a 1J(C,H) NMR spin-spin coupling constant. An experimental and theoretical study
title_full_unstemmed Intramolecular electric field effect on a 1J(C,H) NMR spin-spin coupling constant. An experimental and theoretical study
title_sort intramolecular electric field effect on a 1j(c,h) nmr spin-spin coupling constant. an experimental and theoretical study
url http://hdl.handle.net/20.500.12110/paper_07491581_v37_n3_p227_DeKowalewski
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