Infrared spectrum and UV-induced photochemistry of matrix-isolated 5-methoxy-1-phenyl-1H-tetrazole

Autores
Gomez Zavaglia, Andrea; Reva, I. D.; Frija, L.; Cristiano, M.L.S.; Fausto, R.
Año de publicación
2006
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The molecular structure, vibrational spectra and photochemistry of 5-methoxy-1-phenyl-1H-tetrazole (5MPT) were studied by matrix isolation infrared spectroscopy and DFT(B3LYP)/6-311++G(d,p) calculations. According to the calculations, only one double degenerated-by-symmetry minimum exists in the ground state PES of the compound. In this structure, the dihedral angle between the two rings (phenyl and tetrazole) is ca. 30◦, whereas the methoxyl group stays nearly in the plane of the tetrazole ring. In consonance with the theoretical predictions, only one molecular species was experimentally observed in the as-deposited argon matrices. Theoretical calculations were also used to help in assignment of the experimental spectrum of the compound, the calculated spectrum showing a very good agreement with the experimental data. In situ UVirradiation (λ > 235 nm) of the matrix-isolated 5MPT induced unimolecular decomposition of the compound, which led mainly to production of methylcyanate and phenylazide, this latter further reacting to yield, as final product, 1-aza-1,2,4,6-cycloheptatetraene. 3-Methoxy-1-phenyl-1Hdiazirene was also observed experimentally as minor product, resulting from direct elimination of molecular nitrogen from 5MPT.
Fil: Gomez Zavaglia, Andrea. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos; Argentina
Fil: Reva, I. D.. Universidad de Coimbra; Portugal
Fil: Frija, L.. Universidad de Algarve; Portugal
Fil: Cristiano, M.L.S.. Universidad de Algarve; Portugal
Fil: Fausto, R.. Universidad de Coimbra; Portugal
Materia
FTIR
tetrazole
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:11336/279602
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Infrared spectrum and UV-induced photochemistry of matrix-isolated 5-methoxy-1-phenyl-1H-tetrazoleGomez Zavaglia, AndreaReva, I. D.Frija, L.Cristiano, M.L.S.Fausto, R.FTIRtetrazolehttps://purl.org/becyt/ford/2.11https://purl.org/becyt/ford/2The molecular structure, vibrational spectra and photochemistry of 5-methoxy-1-phenyl-1H-tetrazole (5MPT) were studied by matrix isolation infrared spectroscopy and DFT(B3LYP)/6-311++G(d,p) calculations. According to the calculations, only one double degenerated-by-symmetry minimum exists in the ground state PES of the compound. In this structure, the dihedral angle between the two rings (phenyl and tetrazole) is ca. 30◦, whereas the methoxyl group stays nearly in the plane of the tetrazole ring. In consonance with the theoretical predictions, only one molecular species was experimentally observed in the as-deposited argon matrices. Theoretical calculations were also used to help in assignment of the experimental spectrum of the compound, the calculated spectrum showing a very good agreement with the experimental data. In situ UVirradiation (λ > 235 nm) of the matrix-isolated 5MPT induced unimolecular decomposition of the compound, which led mainly to production of methylcyanate and phenylazide, this latter further reacting to yield, as final product, 1-aza-1,2,4,6-cycloheptatetraene. 3-Methoxy-1-phenyl-1Hdiazirene was also observed experimentally as minor product, resulting from direct elimination of molecular nitrogen from 5MPT.Fil: Gomez Zavaglia, Andrea. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos; ArgentinaFil: Reva, I. D.. Universidad de Coimbra; PortugalFil: Frija, L.. Universidad de Algarve; PortugalFil: Cristiano, M.L.S.. Universidad de Algarve; PortugalFil: Fausto, R.. Universidad de Coimbra; PortugalElsevier Science SA2006-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/279602Gomez Zavaglia, Andrea; Reva, I. D.; Frija, L.; Cristiano, M.L.S.; Fausto, R.; Infrared spectrum and UV-induced photochemistry of matrix-isolated 5-methoxy-1-phenyl-1H-tetrazole; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 180; 1-2; 12-2006; 175-1831010-6030CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2005.10.012info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S1010603005004983info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-02-06T13:30:54Zoai:ri.conicet.gov.ar:11336/279602instacron: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:34982026-02-06 13:30:54.39CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Infrared spectrum and UV-induced photochemistry of matrix-isolated 5-methoxy-1-phenyl-1H-tetrazole
title Infrared spectrum and UV-induced photochemistry of matrix-isolated 5-methoxy-1-phenyl-1H-tetrazole
spellingShingle Infrared spectrum and UV-induced photochemistry of matrix-isolated 5-methoxy-1-phenyl-1H-tetrazole
Gomez Zavaglia, Andrea
FTIR
tetrazole
title_short Infrared spectrum and UV-induced photochemistry of matrix-isolated 5-methoxy-1-phenyl-1H-tetrazole
title_full Infrared spectrum and UV-induced photochemistry of matrix-isolated 5-methoxy-1-phenyl-1H-tetrazole
title_fullStr Infrared spectrum and UV-induced photochemistry of matrix-isolated 5-methoxy-1-phenyl-1H-tetrazole
title_full_unstemmed Infrared spectrum and UV-induced photochemistry of matrix-isolated 5-methoxy-1-phenyl-1H-tetrazole
title_sort Infrared spectrum and UV-induced photochemistry of matrix-isolated 5-methoxy-1-phenyl-1H-tetrazole
dc.creator.none.fl_str_mv Gomez Zavaglia, Andrea
Reva, I. D.
Frija, L.
Cristiano, M.L.S.
Fausto, R.
author Gomez Zavaglia, Andrea
author_facet Gomez Zavaglia, Andrea
Reva, I. D.
Frija, L.
Cristiano, M.L.S.
Fausto, R.
author_role author
author2 Reva, I. D.
Frija, L.
Cristiano, M.L.S.
Fausto, R.
author2_role author
author
author
author
dc.subject.none.fl_str_mv FTIR
tetrazole
topic FTIR
tetrazole
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.11
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv The molecular structure, vibrational spectra and photochemistry of 5-methoxy-1-phenyl-1H-tetrazole (5MPT) were studied by matrix isolation infrared spectroscopy and DFT(B3LYP)/6-311++G(d,p) calculations. According to the calculations, only one double degenerated-by-symmetry minimum exists in the ground state PES of the compound. In this structure, the dihedral angle between the two rings (phenyl and tetrazole) is ca. 30◦, whereas the methoxyl group stays nearly in the plane of the tetrazole ring. In consonance with the theoretical predictions, only one molecular species was experimentally observed in the as-deposited argon matrices. Theoretical calculations were also used to help in assignment of the experimental spectrum of the compound, the calculated spectrum showing a very good agreement with the experimental data. In situ UVirradiation (λ > 235 nm) of the matrix-isolated 5MPT induced unimolecular decomposition of the compound, which led mainly to production of methylcyanate and phenylazide, this latter further reacting to yield, as final product, 1-aza-1,2,4,6-cycloheptatetraene. 3-Methoxy-1-phenyl-1Hdiazirene was also observed experimentally as minor product, resulting from direct elimination of molecular nitrogen from 5MPT.
Fil: Gomez Zavaglia, Andrea. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos; Argentina
Fil: Reva, I. D.. Universidad de Coimbra; Portugal
Fil: Frija, L.. Universidad de Algarve; Portugal
Fil: Cristiano, M.L.S.. Universidad de Algarve; Portugal
Fil: Fausto, R.. Universidad de Coimbra; Portugal
description The molecular structure, vibrational spectra and photochemistry of 5-methoxy-1-phenyl-1H-tetrazole (5MPT) were studied by matrix isolation infrared spectroscopy and DFT(B3LYP)/6-311++G(d,p) calculations. According to the calculations, only one double degenerated-by-symmetry minimum exists in the ground state PES of the compound. In this structure, the dihedral angle between the two rings (phenyl and tetrazole) is ca. 30◦, whereas the methoxyl group stays nearly in the plane of the tetrazole ring. In consonance with the theoretical predictions, only one molecular species was experimentally observed in the as-deposited argon matrices. Theoretical calculations were also used to help in assignment of the experimental spectrum of the compound, the calculated spectrum showing a very good agreement with the experimental data. In situ UVirradiation (λ > 235 nm) of the matrix-isolated 5MPT induced unimolecular decomposition of the compound, which led mainly to production of methylcyanate and phenylazide, this latter further reacting to yield, as final product, 1-aza-1,2,4,6-cycloheptatetraene. 3-Methoxy-1-phenyl-1Hdiazirene was also observed experimentally as minor product, resulting from direct elimination of molecular nitrogen from 5MPT.
publishDate 2006
dc.date.none.fl_str_mv 2006-12
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/11336/279602
Gomez Zavaglia, Andrea; Reva, I. D.; Frija, L.; Cristiano, M.L.S.; Fausto, R.; Infrared spectrum and UV-induced photochemistry of matrix-isolated 5-methoxy-1-phenyl-1H-tetrazole; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 180; 1-2; 12-2006; 175-183
1010-6030
CONICET Digital
CONICET
url http://hdl.handle.net/11336/279602
identifier_str_mv Gomez Zavaglia, Andrea; Reva, I. D.; Frija, L.; Cristiano, M.L.S.; Fausto, R.; Infrared spectrum and UV-induced photochemistry of matrix-isolated 5-methoxy-1-phenyl-1H-tetrazole; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 180; 1-2; 12-2006; 175-183
1010-6030
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.jphotochem.2005.10.012
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S1010603005004983
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 Elsevier Science SA
publisher.none.fl_str_mv Elsevier Science SA
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 12.595271

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