Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles

Autores
Aridoss, Gopalakrishnan; Zhao, Chunqing; Borosky, Gabriela Leonor; Laali, Kenneth K.
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A series of 1-aryl/alkyl-1H-1,2,3,4-tetrazoles, 5-substituted 1H-tetrazoles, and 1,5- and 2,5-disubstituted 1H-tetrazoles were studied by a combination of experimental NMR (natural abundance 15N, 15N/ 1H HMBC, and 13C) and computational GIAO-NMR techniques to explore substituent effects on 15N (and 13C) NMR chemical shifts in the tetrazole (TA) moiety. Computed 15N chemical shifts via GIAO-B3LYP/6-311+G(2d,p) calculations gave satisfactory results in comparison with experimental data. Whereas N-alkylation leads to large 15N chemical shift changes, changes in the N 1-aryl derivatives bearing diverse substituent(s) are generally small except for polar ortho-substituents (COOH, NO 2). Large δδ 15N values were computed in N 1-aryl derivatives for p-COH 2 + and p-OMeH + as extreme examples of electron-withdrawing substituents on a TA moiety. © 2012 American Chemical Society.
Fil: Aridoss, Gopalakrishnan. University of North Florida; Estados Unidos
Fil: Zhao, Chunqing. University of North Florida; Estados Unidos
Fil: Borosky, Gabriela Leonor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Laali, Kenneth K.. University of North Florida; Estados Unidos
Materia
15n Nmr
Tetrazoles
Substituent Effects
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/62479
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazolesAridoss, GopalakrishnanZhao, ChunqingBorosky, Gabriela LeonorLaali, Kenneth K.15n NmrTetrazolesSubstituent Effectshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of 1-aryl/alkyl-1H-1,2,3,4-tetrazoles, 5-substituted 1H-tetrazoles, and 1,5- and 2,5-disubstituted 1H-tetrazoles were studied by a combination of experimental NMR (natural abundance 15N, 15N/ 1H HMBC, and 13C) and computational GIAO-NMR techniques to explore substituent effects on 15N (and 13C) NMR chemical shifts in the tetrazole (TA) moiety. Computed 15N chemical shifts via GIAO-B3LYP/6-311+G(2d,p) calculations gave satisfactory results in comparison with experimental data. Whereas N-alkylation leads to large 15N chemical shift changes, changes in the N 1-aryl derivatives bearing diverse substituent(s) are generally small except for polar ortho-substituents (COOH, NO 2). Large δδ 15N values were computed in N 1-aryl derivatives for p-COH 2 + and p-OMeH + as extreme examples of electron-withdrawing substituents on a TA moiety. © 2012 American Chemical Society.Fil: Aridoss, Gopalakrishnan. University of North Florida; Estados UnidosFil: Zhao, Chunqing. University of North Florida; Estados UnidosFil: Borosky, Gabriela Leonor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Laali, Kenneth K.. University of North Florida; Estados UnidosAmerican Chemical Society2012-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/62479Aridoss, Gopalakrishnan; Zhao, Chunqing; Borosky, Gabriela Leonor; Laali, Kenneth K.; Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles; American Chemical Society; Journal of Organic Chemistry; 77; 8; 4-2012; 4152-41550022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/jo300242sinfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jo300242sinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-05T09:36:27Zoai:ri.conicet.gov.ar:11336/62479instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-11-05 09:36:28.183CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles
title Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles
spellingShingle Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles
Aridoss, Gopalakrishnan
15n Nmr
Tetrazoles
Substituent Effects
title_short Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles
title_full Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles
title_fullStr Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles
title_full_unstemmed Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles
title_sort Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles
dc.creator.none.fl_str_mv Aridoss, Gopalakrishnan
Zhao, Chunqing
Borosky, Gabriela Leonor
Laali, Kenneth K.
author Aridoss, Gopalakrishnan
author_facet Aridoss, Gopalakrishnan
Zhao, Chunqing
Borosky, Gabriela Leonor
Laali, Kenneth K.
author_role author
author2 Zhao, Chunqing
Borosky, Gabriela Leonor
Laali, Kenneth K.
author2_role author
author
author
dc.subject.none.fl_str_mv 15n Nmr
Tetrazoles
Substituent Effects
topic 15n Nmr
Tetrazoles
Substituent Effects
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A series of 1-aryl/alkyl-1H-1,2,3,4-tetrazoles, 5-substituted 1H-tetrazoles, and 1,5- and 2,5-disubstituted 1H-tetrazoles were studied by a combination of experimental NMR (natural abundance 15N, 15N/ 1H HMBC, and 13C) and computational GIAO-NMR techniques to explore substituent effects on 15N (and 13C) NMR chemical shifts in the tetrazole (TA) moiety. Computed 15N chemical shifts via GIAO-B3LYP/6-311+G(2d,p) calculations gave satisfactory results in comparison with experimental data. Whereas N-alkylation leads to large 15N chemical shift changes, changes in the N 1-aryl derivatives bearing diverse substituent(s) are generally small except for polar ortho-substituents (COOH, NO 2). Large δδ 15N values were computed in N 1-aryl derivatives for p-COH 2 + and p-OMeH + as extreme examples of electron-withdrawing substituents on a TA moiety. © 2012 American Chemical Society.
Fil: Aridoss, Gopalakrishnan. University of North Florida; Estados Unidos
Fil: Zhao, Chunqing. University of North Florida; Estados Unidos
Fil: Borosky, Gabriela Leonor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Laali, Kenneth K.. University of North Florida; Estados Unidos
description A series of 1-aryl/alkyl-1H-1,2,3,4-tetrazoles, 5-substituted 1H-tetrazoles, and 1,5- and 2,5-disubstituted 1H-tetrazoles were studied by a combination of experimental NMR (natural abundance 15N, 15N/ 1H HMBC, and 13C) and computational GIAO-NMR techniques to explore substituent effects on 15N (and 13C) NMR chemical shifts in the tetrazole (TA) moiety. Computed 15N chemical shifts via GIAO-B3LYP/6-311+G(2d,p) calculations gave satisfactory results in comparison with experimental data. Whereas N-alkylation leads to large 15N chemical shift changes, changes in the N 1-aryl derivatives bearing diverse substituent(s) are generally small except for polar ortho-substituents (COOH, NO 2). Large δδ 15N values were computed in N 1-aryl derivatives for p-COH 2 + and p-OMeH + as extreme examples of electron-withdrawing substituents on a TA moiety. © 2012 American Chemical Society.
publishDate 2012
dc.date.none.fl_str_mv 2012-04
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/62479
Aridoss, Gopalakrishnan; Zhao, Chunqing; Borosky, Gabriela Leonor; Laali, Kenneth K.; Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles; American Chemical Society; Journal of Organic Chemistry; 77; 8; 4-2012; 4152-4155
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/62479
identifier_str_mv Aridoss, Gopalakrishnan; Zhao, Chunqing; Borosky, Gabriela Leonor; Laali, Kenneth K.; Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles; American Chemical Society; Journal of Organic Chemistry; 77; 8; 4-2012; 4152-4155
0022-3263
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/jo300242s
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jo300242s
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.087074

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