UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone

Autores
Frija, L. M. T.; Reva, I. D.; Gomez Zavaglia, Andrea; Cristiano, M. L. S.; Fausto, R.
Año de publicación
2007
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The photochemistry and molecular structure of 1-phenyl-4-allyl-tetrazolone (PAT) was studied by FT-IR matrix isolation spectroscopy and DFT(B3LYP)/6-311++G(d,p) calculations. The spectrum of matrix-isolated PAT monomers agrees well with the sum spectrum of three conformers predicted theoretically. UV irradiation (lambda > 235 nm) of matrix-isolated PAT induces three types of photofragmentation: (1) production of phenylazide and allyl-isocyanate, with phenylazide then losing N(2) to yield 1-aza-1,2,4,6-cycloheptatetraene; (2) formation of phenyl-isocyanate and allylazide; (3) N(2) elimination leading to formation of 1-allyl-2-phenyldiaziridin-3-one; this compound partially reacts further to form 1-allyl-1H-benzoimidazol-2(3H)-one. The observed photochemistry of the matrix-isolated PAT is distinct from the preferred photochemical fragmentation in solution, where 3,4-dihydro-3-phenylpyrimidin-2(1H)-one is produced as the primary photoproduct.
Fil: Frija, L. M. T.. Universidad de Algarve; Portugal
Fil: Reva, I. D.. Universidad de Coimbra; Portugal
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: Cristiano, M. L. S.. Universidad de Algarve; Portugal
Fil: Fausto, R.. Universidad de Coimbra; Portugal
Materia
Tetrazoles
FTIR
Matrix isolation spectroscopy
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:11336/110205
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazoloneFrija, L. M. T.Reva, I. D.Gomez Zavaglia, AndreaCristiano, M. L. S.Fausto, R.TetrazolesFTIRMatrix isolation spectroscopyhttps://purl.org/becyt/ford/2.11https://purl.org/becyt/ford/2The photochemistry and molecular structure of 1-phenyl-4-allyl-tetrazolone (PAT) was studied by FT-IR matrix isolation spectroscopy and DFT(B3LYP)/6-311++G(d,p) calculations. The spectrum of matrix-isolated PAT monomers agrees well with the sum spectrum of three conformers predicted theoretically. UV irradiation (lambda > 235 nm) of matrix-isolated PAT induces three types of photofragmentation: (1) production of phenylazide and allyl-isocyanate, with phenylazide then losing N(2) to yield 1-aza-1,2,4,6-cycloheptatetraene; (2) formation of phenyl-isocyanate and allylazide; (3) N(2) elimination leading to formation of 1-allyl-2-phenyldiaziridin-3-one; this compound partially reacts further to form 1-allyl-1H-benzoimidazol-2(3H)-one. The observed photochemistry of the matrix-isolated PAT is distinct from the preferred photochemical fragmentation in solution, where 3,4-dihydro-3-phenylpyrimidin-2(1H)-one is produced as the primary photoproduct.Fil: Frija, L. M. T.. Universidad de Algarve; PortugalFil: Reva, I. D.. Universidad de Coimbra; PortugalFil: 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: Cristiano, M. L. S.. Universidad de Algarve; PortugalFil: Fausto, R.. Universidad de Coimbra; PortugalRoyal Society of Chemistry2007-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/110205Frija, L. M. T.; Reva, I. D.; Gomez Zavaglia, Andrea; Cristiano, M. L. S.; Fausto, R.; UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 6; 11; 12-2007; 1170-11761474-905XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2007/pp/b703961a/unauth#!divAbstractinfo:eu-repo/semantics/altIdentifier/doi/10.1039/b703961ainfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:19:03Zoai:ri.conicet.gov.ar:11336/110205instacron: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 10:19:03.601CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone
title UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone
spellingShingle UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone
Frija, L. M. T.
Tetrazoles
FTIR
Matrix isolation spectroscopy
title_short UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone
title_full UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone
title_fullStr UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone
title_full_unstemmed UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone
title_sort UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone
dc.creator.none.fl_str_mv Frija, L. M. T.
Reva, I. D.
Gomez Zavaglia, Andrea
Cristiano, M. L. S.
Fausto, R.
author Frija, L. M. T.
author_facet Frija, L. M. T.
Reva, I. D.
Gomez Zavaglia, Andrea
Cristiano, M. L. S.
Fausto, R.
author_role author
author2 Reva, I. D.
Gomez Zavaglia, Andrea
Cristiano, M. L. S.
Fausto, R.
author2_role author
author
author
author
dc.subject.none.fl_str_mv Tetrazoles
FTIR
Matrix isolation spectroscopy
topic Tetrazoles
FTIR
Matrix isolation spectroscopy
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 photochemistry and molecular structure of 1-phenyl-4-allyl-tetrazolone (PAT) was studied by FT-IR matrix isolation spectroscopy and DFT(B3LYP)/6-311++G(d,p) calculations. The spectrum of matrix-isolated PAT monomers agrees well with the sum spectrum of three conformers predicted theoretically. UV irradiation (lambda > 235 nm) of matrix-isolated PAT induces three types of photofragmentation: (1) production of phenylazide and allyl-isocyanate, with phenylazide then losing N(2) to yield 1-aza-1,2,4,6-cycloheptatetraene; (2) formation of phenyl-isocyanate and allylazide; (3) N(2) elimination leading to formation of 1-allyl-2-phenyldiaziridin-3-one; this compound partially reacts further to form 1-allyl-1H-benzoimidazol-2(3H)-one. The observed photochemistry of the matrix-isolated PAT is distinct from the preferred photochemical fragmentation in solution, where 3,4-dihydro-3-phenylpyrimidin-2(1H)-one is produced as the primary photoproduct.
Fil: Frija, L. M. T.. Universidad de Algarve; Portugal
Fil: Reva, I. D.. Universidad de Coimbra; Portugal
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: Cristiano, M. L. S.. Universidad de Algarve; Portugal
Fil: Fausto, R.. Universidad de Coimbra; Portugal
description The photochemistry and molecular structure of 1-phenyl-4-allyl-tetrazolone (PAT) was studied by FT-IR matrix isolation spectroscopy and DFT(B3LYP)/6-311++G(d,p) calculations. The spectrum of matrix-isolated PAT monomers agrees well with the sum spectrum of three conformers predicted theoretically. UV irradiation (lambda > 235 nm) of matrix-isolated PAT induces three types of photofragmentation: (1) production of phenylazide and allyl-isocyanate, with phenylazide then losing N(2) to yield 1-aza-1,2,4,6-cycloheptatetraene; (2) formation of phenyl-isocyanate and allylazide; (3) N(2) elimination leading to formation of 1-allyl-2-phenyldiaziridin-3-one; this compound partially reacts further to form 1-allyl-1H-benzoimidazol-2(3H)-one. The observed photochemistry of the matrix-isolated PAT is distinct from the preferred photochemical fragmentation in solution, where 3,4-dihydro-3-phenylpyrimidin-2(1H)-one is produced as the primary photoproduct.
publishDate 2007
dc.date.none.fl_str_mv 2007-12
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/11336/110205
Frija, L. M. T.; Reva, I. D.; Gomez Zavaglia, Andrea; Cristiano, M. L. S.; Fausto, R.; UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 6; 11; 12-2007; 1170-1176
1474-905X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/110205
identifier_str_mv Frija, L. M. T.; Reva, I. D.; Gomez Zavaglia, Andrea; Cristiano, M. L. S.; Fausto, R.; UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 6; 11; 12-2007; 1170-1176
1474-905X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2007/pp/b703961a/unauth#!divAbstract
info:eu-repo/semantics/altIdentifier/doi/10.1039/b703961a
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 Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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 13.069144

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