A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester

Autores
Saeed, Aamer; Qasim, Muhammad; Hussain, Majid; Flörke, Ulrich; Erben, Mauricio Federico
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The tautomeric and conformational properties of a new tetrazole derivative are studied in a combined approach that includes the analysis of the experimental vibrational data together with theoretical calculation methods, especially in terms of natural bond orbital (NBO) population analysis. Moreover, the molecular and crystal structure was determined by single crystal X-ray diffraction. The compound crystallized as the 2-tautomeric form, monoclinic space group P21/c with Z = 4, a = 10.0630(14), b = 8.2879(11), c = 12.8375(18) Å, b = 105.546(3), V = 1031.5(2) Å3. The tetrazole and phenyl rings are coplanar with the acetate group oriented perpendicular to the plane. The NBO analysis showed that delocalizing interactions of the lpp(N2) lone pair orbital contributes to a strong resonance interactions with both adjacent antibonding orbitals of the tetrazole group.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Qasim, Muhammad. Quaid-I-Azam University; Pakistán
Fil: Hussain, Majid. Quaid-I-Azam University; Pakistán
Fil: Flörke, Ulrich. Universitat Paderborn; Alemania
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Materia
Tetrazole
Vibrational Spectroscopy
Quantum Chemical Calculations
Crystal Structure
Conformational Analysis
Tautomerism
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:11336/48249
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/48249
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl esterSaeed, AamerQasim, MuhammadHussain, MajidFlörke, UlrichErben, Mauricio FedericoTetrazoleVibrational SpectroscopyQuantum Chemical CalculationsCrystal StructureConformational AnalysisTautomerismhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The tautomeric and conformational properties of a new tetrazole derivative are studied in a combined approach that includes the analysis of the experimental vibrational data together with theoretical calculation methods, especially in terms of natural bond orbital (NBO) population analysis. Moreover, the molecular and crystal structure was determined by single crystal X-ray diffraction. The compound crystallized as the 2-tautomeric form, monoclinic space group P21/c with Z = 4, a = 10.0630(14), b = 8.2879(11), c = 12.8375(18) Å, b = 105.546(3), V = 1031.5(2) Å3. The tetrazole and phenyl rings are coplanar with the acetate group oriented perpendicular to the plane. The NBO analysis showed that delocalizing interactions of the lpp(N2) lone pair orbital contributes to a strong resonance interactions with both adjacent antibonding orbitals of the tetrazole group.Fil: Saeed, Aamer. Quaid-I-Azam University; PakistánFil: Qasim, Muhammad. Quaid-I-Azam University; PakistánFil: Hussain, Majid. Quaid-I-Azam University; PakistánFil: Flörke, Ulrich. Universitat Paderborn; AlemaniaFil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaPergamon-Elsevier Science Ltd2015-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/48249Saeed, Aamer; Qasim, Muhammad; Hussain, Majid; Flörke, Ulrich; Erben, Mauricio Federico; A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester; Pergamon-Elsevier Science Ltd; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 150; 11-2015; 1-81386-1425CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2015.05.046info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1386142515006356info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:18:03Zoai:ri.conicet.gov.ar:11336/48249instacron: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:34982025-09-29 10:18:03.277CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester
title A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester
spellingShingle A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester
Saeed, Aamer
Tetrazole
Vibrational Spectroscopy
Quantum Chemical Calculations
Crystal Structure
Conformational Analysis
Tautomerism
title_short A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester
title_full A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester
title_fullStr A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester
title_full_unstemmed A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester
title_sort A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester
dc.creator.none.fl_str_mv Saeed, Aamer
Qasim, Muhammad
Hussain, Majid
Flörke, Ulrich
Erben, Mauricio Federico
author Saeed, Aamer
author_facet Saeed, Aamer
Qasim, Muhammad
Hussain, Majid
Flörke, Ulrich
Erben, Mauricio Federico
author_role author
author2 Qasim, Muhammad
Hussain, Majid
Flörke, Ulrich
Erben, Mauricio Federico
author2_role author
author
author
author
dc.subject.none.fl_str_mv Tetrazole
Vibrational Spectroscopy
Quantum Chemical Calculations
Crystal Structure
Conformational Analysis
Tautomerism
topic Tetrazole
Vibrational Spectroscopy
Quantum Chemical Calculations
Crystal Structure
Conformational Analysis
Tautomerism
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The tautomeric and conformational properties of a new tetrazole derivative are studied in a combined approach that includes the analysis of the experimental vibrational data together with theoretical calculation methods, especially in terms of natural bond orbital (NBO) population analysis. Moreover, the molecular and crystal structure was determined by single crystal X-ray diffraction. The compound crystallized as the 2-tautomeric form, monoclinic space group P21/c with Z = 4, a = 10.0630(14), b = 8.2879(11), c = 12.8375(18) Å, b = 105.546(3), V = 1031.5(2) Å3. The tetrazole and phenyl rings are coplanar with the acetate group oriented perpendicular to the plane. The NBO analysis showed that delocalizing interactions of the lpp(N2) lone pair orbital contributes to a strong resonance interactions with both adjacent antibonding orbitals of the tetrazole group.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Qasim, Muhammad. Quaid-I-Azam University; Pakistán
Fil: Hussain, Majid. Quaid-I-Azam University; Pakistán
Fil: Flörke, Ulrich. Universitat Paderborn; Alemania
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
description The tautomeric and conformational properties of a new tetrazole derivative are studied in a combined approach that includes the analysis of the experimental vibrational data together with theoretical calculation methods, especially in terms of natural bond orbital (NBO) population analysis. Moreover, the molecular and crystal structure was determined by single crystal X-ray diffraction. The compound crystallized as the 2-tautomeric form, monoclinic space group P21/c with Z = 4, a = 10.0630(14), b = 8.2879(11), c = 12.8375(18) Å, b = 105.546(3), V = 1031.5(2) Å3. The tetrazole and phenyl rings are coplanar with the acetate group oriented perpendicular to the plane. The NBO analysis showed that delocalizing interactions of the lpp(N2) lone pair orbital contributes to a strong resonance interactions with both adjacent antibonding orbitals of the tetrazole group.
publishDate 2015
dc.date.none.fl_str_mv 2015-11
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/11336/48249
Saeed, Aamer; Qasim, Muhammad; Hussain, Majid; Flörke, Ulrich; Erben, Mauricio Federico; A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester; Pergamon-Elsevier Science Ltd; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 150; 11-2015; 1-8
1386-1425
CONICET Digital
CONICET
url http://hdl.handle.net/11336/48249
identifier_str_mv Saeed, Aamer; Qasim, Muhammad; Hussain, Majid; Flörke, Ulrich; Erben, Mauricio Federico; A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester; Pergamon-Elsevier Science Ltd; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 150; 11-2015; 1-8
1386-1425
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2015.05.046
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1386142515006356
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 Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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 13.070432

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