Unexpected valence bond isomerization of [1,2,4]triazolo[3,4-c][1,2,4]benzotriazines under flash vacuum pyrolytic (fvp) conditions

Autores
Peláez, Walter José; Yranzo, Gloria Inés; Gróf, Csilla; Riedl, Zsuzsanna; Hajós, György
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Flash vacuum pyrolysis (fvp) of some substituted [1,2,4]triazolo[3,4-c][1,2,4]benzotriazine derivatives (1a–d) has been studied between 450 and 600 8C. The only transformation observed up to 525 8C was the unexpected valence bond isomerization of the angularly fused starting compounds to the isomeric linearly fused [1,2,4]triazolo[4,3-b][1,2,4]benzotriazine derivatives (9a–d), whereas at higher temperatures fragmentation products such as aromatic nitriles were also formed. Kinetic measurements revealed negative entropies of activation in the isomerization process, which suggest a concerted ring closure reaction to an intermediate antiaromatic diazirine. Reversibiblity of the title isomerization reaction was also proved by FVP experiments.
Fil: Peláez, Walter José. 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: Yranzo, Gloria Inés. 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: Gróf, Csilla. Hungarian Academy of Sciences; Hungría
Fil: Riedl, Zsuzsanna. Hungarian Academy of Sciences; Hungría
Fil: Hajós, György. Hungarian Academy of Sciences; Hungría
Materia
Pyrolysis
Triazines
heterocycles
Arrhenius
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:11336/241389
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/241389
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Unexpected valence bond isomerization of [1,2,4]triazolo[3,4-c][1,2,4]benzotriazines under flash vacuum pyrolytic (fvp) conditionsPeláez, Walter JoséYranzo, Gloria InésGróf, CsillaRiedl, ZsuzsannaHajós, GyörgyPyrolysisTriazinesheterocyclesArrheniushttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Flash vacuum pyrolysis (fvp) of some substituted [1,2,4]triazolo[3,4-c][1,2,4]benzotriazine derivatives (1a–d) has been studied between 450 and 600 8C. The only transformation observed up to 525 8C was the unexpected valence bond isomerization of the angularly fused starting compounds to the isomeric linearly fused [1,2,4]triazolo[4,3-b][1,2,4]benzotriazine derivatives (9a–d), whereas at higher temperatures fragmentation products such as aromatic nitriles were also formed. Kinetic measurements revealed negative entropies of activation in the isomerization process, which suggest a concerted ring closure reaction to an intermediate antiaromatic diazirine. Reversibiblity of the title isomerization reaction was also proved by FVP experiments.Fil: Peláez, Walter José. 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: Yranzo, Gloria Inés. 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: Gróf, Csilla. Hungarian Academy of Sciences; HungríaFil: Riedl, Zsuzsanna. Hungarian Academy of Sciences; HungríaFil: Hajós, György. Hungarian Academy of Sciences; HungríaPergamon-Elsevier Science Ltd2005-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/241389Peláez, Walter José; Yranzo, Gloria Inés; Gróf, Csilla; Riedl, Zsuzsanna; Hajós, György; Unexpected valence bond isomerization of [1,2,4]triazolo[3,4-c][1,2,4]benzotriazines under flash vacuum pyrolytic (fvp) conditions; Pergamon-Elsevier Science Ltd; Tetrahedron; 61; 31; 8-2005; 7489-74980040-4020CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040402005008732info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2005.05.047info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:09:41Zoai:ri.conicet.gov.ar:11336/241389instacron: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 10:09:41.742CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Unexpected valence bond isomerization of [1,2,4]triazolo[3,4-c][1,2,4]benzotriazines under flash vacuum pyrolytic (fvp) conditions
title Unexpected valence bond isomerization of [1,2,4]triazolo[3,4-c][1,2,4]benzotriazines under flash vacuum pyrolytic (fvp) conditions
spellingShingle Unexpected valence bond isomerization of [1,2,4]triazolo[3,4-c][1,2,4]benzotriazines under flash vacuum pyrolytic (fvp) conditions
Peláez, Walter José
Pyrolysis
Triazines
heterocycles
Arrhenius
title_short Unexpected valence bond isomerization of [1,2,4]triazolo[3,4-c][1,2,4]benzotriazines under flash vacuum pyrolytic (fvp) conditions
title_full Unexpected valence bond isomerization of [1,2,4]triazolo[3,4-c][1,2,4]benzotriazines under flash vacuum pyrolytic (fvp) conditions
title_fullStr Unexpected valence bond isomerization of [1,2,4]triazolo[3,4-c][1,2,4]benzotriazines under flash vacuum pyrolytic (fvp) conditions
title_full_unstemmed Unexpected valence bond isomerization of [1,2,4]triazolo[3,4-c][1,2,4]benzotriazines under flash vacuum pyrolytic (fvp) conditions
title_sort Unexpected valence bond isomerization of [1,2,4]triazolo[3,4-c][1,2,4]benzotriazines under flash vacuum pyrolytic (fvp) conditions
dc.creator.none.fl_str_mv Peláez, Walter José
Yranzo, Gloria Inés
Gróf, Csilla
Riedl, Zsuzsanna
Hajós, György
author Peláez, Walter José
author_facet Peláez, Walter José
Yranzo, Gloria Inés
Gróf, Csilla
Riedl, Zsuzsanna
Hajós, György
author_role author
author2 Yranzo, Gloria Inés
Gróf, Csilla
Riedl, Zsuzsanna
Hajós, György
author2_role author
author
author
author
dc.subject.none.fl_str_mv Pyrolysis
Triazines
heterocycles
Arrhenius
topic Pyrolysis
Triazines
heterocycles
Arrhenius
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Flash vacuum pyrolysis (fvp) of some substituted [1,2,4]triazolo[3,4-c][1,2,4]benzotriazine derivatives (1a–d) has been studied between 450 and 600 8C. The only transformation observed up to 525 8C was the unexpected valence bond isomerization of the angularly fused starting compounds to the isomeric linearly fused [1,2,4]triazolo[4,3-b][1,2,4]benzotriazine derivatives (9a–d), whereas at higher temperatures fragmentation products such as aromatic nitriles were also formed. Kinetic measurements revealed negative entropies of activation in the isomerization process, which suggest a concerted ring closure reaction to an intermediate antiaromatic diazirine. Reversibiblity of the title isomerization reaction was also proved by FVP experiments.
Fil: Peláez, Walter José. 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: Yranzo, Gloria Inés. 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: Gróf, Csilla. Hungarian Academy of Sciences; Hungría
Fil: Riedl, Zsuzsanna. Hungarian Academy of Sciences; Hungría
Fil: Hajós, György. Hungarian Academy of Sciences; Hungría
description Flash vacuum pyrolysis (fvp) of some substituted [1,2,4]triazolo[3,4-c][1,2,4]benzotriazine derivatives (1a–d) has been studied between 450 and 600 8C. The only transformation observed up to 525 8C was the unexpected valence bond isomerization of the angularly fused starting compounds to the isomeric linearly fused [1,2,4]triazolo[4,3-b][1,2,4]benzotriazine derivatives (9a–d), whereas at higher temperatures fragmentation products such as aromatic nitriles were also formed. Kinetic measurements revealed negative entropies of activation in the isomerization process, which suggest a concerted ring closure reaction to an intermediate antiaromatic diazirine. Reversibiblity of the title isomerization reaction was also proved by FVP experiments.
publishDate 2005
dc.date.none.fl_str_mv 2005-08
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/11336/241389
Peláez, Walter José; Yranzo, Gloria Inés; Gróf, Csilla; Riedl, Zsuzsanna; Hajós, György; Unexpected valence bond isomerization of [1,2,4]triazolo[3,4-c][1,2,4]benzotriazines under flash vacuum pyrolytic (fvp) conditions; Pergamon-Elsevier Science Ltd; Tetrahedron; 61; 31; 8-2005; 7489-7498
0040-4020
CONICET Digital
CONICET
url http://hdl.handle.net/11336/241389
identifier_str_mv Peláez, Walter José; Yranzo, Gloria Inés; Gróf, Csilla; Riedl, Zsuzsanna; Hajós, György; Unexpected valence bond isomerization of [1,2,4]triazolo[3,4-c][1,2,4]benzotriazines under flash vacuum pyrolytic (fvp) conditions; Pergamon-Elsevier Science Ltd; Tetrahedron; 61; 31; 8-2005; 7489-7498
0040-4020
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://www.sciencedirect.com/science/article/pii/S0040402005008732
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2005.05.047
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
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 13.13397

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