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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/110205
Ver los metadatos del registro completo
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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 Técnicas2025-09-03T10:02:46Zoai: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:34982025-09-03 10:02:46.925CONICET 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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1842269772623904768 |
score |
13.13397 |