Theoretical comparison of proximate peri and ortho substituent effects on proton chemical shifts

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The magnetic shielding of the peri proton in 1-X-naphthalenes and the ortho proton in 1-X-benzenes were studied and compared. The respective distances between the substituent group X and the peri proton in 1-X-naphthalenes or the ortho proton in 1-X-benzenes are very similar, but the substituent che...

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Autores principales: Herr, T., Ferraro, M.B., Contreras, R.H.
Formato: JOUR
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_01661280_v254_nC_p253_Herr
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_01661280_v254_nC_p253_Herr2023-10-03T15:03:18Z Theoretical comparison of proximate peri and ortho substituent effects on proton chemical shifts Herr, T. Ferraro, M.B. Contreras, R.H. The magnetic shielding of the peri proton in 1-X-naphthalenes and the ortho proton in 1-X-benzenes were studied and compared. The respective distances between the substituent group X and the peri proton in 1-X-naphthalenes or the ortho proton in 1-X-benzenes are very similar, but the substituent chemical shifts may be very different, depending on the substituent. In 1-X-naphthalenes the C-H8 (peri proton) bond takes an orientation which is different from that adopted by the C-H2 (ortho proton) bond in 1-X-benzenes. This may be responsible for the observed differences, so we evaluated the "throughspace" contributions to the magnetic shielding in both cases within the IPPP-CHF-INDO-GIAO (inner projections of the polarization propagator, coupled Hartree-Fock, semiempirical INDO wave function, gauge invariant atomic orbitals) approach to investigate the extent to which these effects determine the experimental trends. © 1992. Fil:Herr, T. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ferraro, M.B. 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_01661280_v254_nC_p253_Herr
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 magnetic shielding of the peri proton in 1-X-naphthalenes and the ortho proton in 1-X-benzenes were studied and compared. The respective distances between the substituent group X and the peri proton in 1-X-naphthalenes or the ortho proton in 1-X-benzenes are very similar, but the substituent chemical shifts may be very different, depending on the substituent. In 1-X-naphthalenes the C-H8 (peri proton) bond takes an orientation which is different from that adopted by the C-H2 (ortho proton) bond in 1-X-benzenes. This may be responsible for the observed differences, so we evaluated the "throughspace" contributions to the magnetic shielding in both cases within the IPPP-CHF-INDO-GIAO (inner projections of the polarization propagator, coupled Hartree-Fock, semiempirical INDO wave function, gauge invariant atomic orbitals) approach to investigate the extent to which these effects determine the experimental trends. © 1992.
format JOUR
author Herr, T.
Ferraro, M.B.
Contreras, R.H.
spellingShingle Herr, T.
Ferraro, M.B.
Contreras, R.H.
Theoretical comparison of proximate peri and ortho substituent effects on proton chemical shifts
author_facet Herr, T.
Ferraro, M.B.
Contreras, R.H.
author_sort Herr, T.
title Theoretical comparison of proximate peri and ortho substituent effects on proton chemical shifts
title_short Theoretical comparison of proximate peri and ortho substituent effects on proton chemical shifts
title_full Theoretical comparison of proximate peri and ortho substituent effects on proton chemical shifts
title_fullStr Theoretical comparison of proximate peri and ortho substituent effects on proton chemical shifts
title_full_unstemmed Theoretical comparison of proximate peri and ortho substituent effects on proton chemical shifts
title_sort theoretical comparison of proximate peri and ortho substituent effects on proton chemical shifts
url http://hdl.handle.net/20.500.12110/paper_01661280_v254_nC_p253_Herr
work_keys_str_mv AT herrt theoreticalcomparisonofproximateperiandorthosubstituenteffectsonprotonchemicalshifts
AT ferraromb theoreticalcomparisonofproximateperiandorthosubstituenteffectsonprotonchemicalshifts
AT contrerasrh theoreticalcomparisonofproximateperiandorthosubstituenteffectsonprotonchemicalshifts
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