Analysis of long‐range through‐space couplings via an intramolecular hydrogen bond

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2‐Fluorobenzamide and its N‐methyl derivative show spin‐spin couplings between the aromatic fluorine and the nitrogen and carbon of the amide group, which are absent in the corresponding N,N‐dimethylamide. The N‐methyl compound, in which there is a hydrogen bond between the fluorine and the amide hy...

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Autores principales: Rae, I.D., Weigold, J.A., Contreras, R.H., Biekofsky, R.R.
Formato: JOUR
Materias:
IPPP–INDO calculations
Long‐range coupling
Through‐space coupling
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_07491581_v31_n9_p836_Rae
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_07491581_v31_n9_p836_Rae
record_format dspace
spelling todo:paper_07491581_v31_n9_p836_Rae2023-10-03T15:39:21Z Analysis of long‐range through‐space couplings via an intramolecular hydrogen bond Rae, I.D. Weigold, J.A. Contreras, R.H. Biekofsky, R.R. IPPP–INDO calculations Long‐range coupling Through‐space coupling 2‐Fluorobenzamide and its N‐methyl derivative show spin‐spin couplings between the aromatic fluorine and the nitrogen and carbon of the amide group, which are absent in the corresponding N,N‐dimethylamide. The N‐methyl compound, in which there is a hydrogen bond between the fluorine and the amide hydrogen, also shows fluorine couplings to the nuclei of the methyl group, and these are diminished for solutions of the amide in polar solvents. Such couplings are absent in the N,N‐dimethylamide, which does, however, show fluorine couplings to the proximate methyl group. Calculations at the INDO level employing the IPPP method give reasonable agreement with the magnitudes of the observed 4J(F,N) values in the N‐methylamide and show that the Fermi contact contributions are dominant and that the spin information is transmitted mainly through the hydrogen bond. Copyright © 1993 John Wiley & Sons, Ltd. Fil:Contreras, R.H. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Biekofsky, R.R. 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_v31_n9_p836_Rae
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic IPPP–INDO calculations
Long‐range coupling
Through‐space coupling
spellingShingle IPPP–INDO calculations
Long‐range coupling
Through‐space coupling
Rae, I.D.
Weigold, J.A.
Contreras, R.H.
Biekofsky, R.R.
Analysis of long‐range through‐space couplings via an intramolecular hydrogen bond
topic_facet IPPP–INDO calculations
Long‐range coupling
Through‐space coupling
description 2‐Fluorobenzamide and its N‐methyl derivative show spin‐spin couplings between the aromatic fluorine and the nitrogen and carbon of the amide group, which are absent in the corresponding N,N‐dimethylamide. The N‐methyl compound, in which there is a hydrogen bond between the fluorine and the amide hydrogen, also shows fluorine couplings to the nuclei of the methyl group, and these are diminished for solutions of the amide in polar solvents. Such couplings are absent in the N,N‐dimethylamide, which does, however, show fluorine couplings to the proximate methyl group. Calculations at the INDO level employing the IPPP method give reasonable agreement with the magnitudes of the observed 4J(F,N) values in the N‐methylamide and show that the Fermi contact contributions are dominant and that the spin information is transmitted mainly through the hydrogen bond. Copyright © 1993 John Wiley & Sons, Ltd.
format JOUR
author Rae, I.D.
Weigold, J.A.
Contreras, R.H.
Biekofsky, R.R.
author_facet Rae, I.D.
Weigold, J.A.
Contreras, R.H.
Biekofsky, R.R.
author_sort Rae, I.D.
title Analysis of long‐range through‐space couplings via an intramolecular hydrogen bond
title_short Analysis of long‐range through‐space couplings via an intramolecular hydrogen bond
title_full Analysis of long‐range through‐space couplings via an intramolecular hydrogen bond
title_fullStr Analysis of long‐range through‐space couplings via an intramolecular hydrogen bond
title_full_unstemmed Analysis of long‐range through‐space couplings via an intramolecular hydrogen bond
title_sort analysis of long‐range through‐space couplings via an intramolecular hydrogen bond
url http://hdl.handle.net/20.500.12110/paper_07491581_v31_n9_p836_Rae
work_keys_str_mv AT raeid analysisoflongrangethroughspacecouplingsviaanintramolecularhydrogenbond
AT weigoldja analysisoflongrangethroughspacecouplingsviaanintramolecularhydrogenbond
AT contrerasrh analysisoflongrangethroughspacecouplingsviaanintramolecularhydrogenbond
AT biekofskyrr analysisoflongrangethroughspacecouplingsviaanintramolecularhydrogenbond
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