The mechanism of the reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford 2-pyrazolines (4,5-dihydro-1H-pyrazoles): experimental and theoretical results

The reaction of hydrazines with a,b-unsaturated carbonyl compounds to afford 2-pyrazolines was studied using a dissymmetric chalcone (phenyl/p-tolyl) and three hydrazines, hydrazine itself, phenylhydrazine and thiosemicarbazide. Several products were identified, and some reaction paths established t...

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Detalles Bibliográficos
Autores: Hoz Ayuso, Antonio de la, Alkorta, Ibón, Elguero, José
Tipo de recurso: artículo
Fecha de publicación:2021
País:España
Institución:Universidad de Castilla-La Mancha
Repositorio:RUIdeRA. Repositorio Institucional de la UCLM
OAI Identifier:oai:ruidera.uclm.es:10578/38427
Acceso en línea:https://hdl.handle.net/10578/38427
Access Level:acceso embargado
Palabra clave:Pyrazolines, Dihydropyrazoles, Hydrazones, IRC, GIAO, NMR
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spelling The mechanism of the reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford 2-pyrazolines (4,5-dihydro-1H-pyrazoles): experimental and theoretical resultsHoz Ayuso, Antonio de laAlkorta, IbónElguero, JoséPyrazolines, Dihydropyrazoles, Hydrazones, IRC, GIAO, NMRThe reaction of hydrazines with a,b-unsaturated carbonyl compounds to afford 2-pyrazolines was studied using a dissymmetric chalcone (phenyl/p-tolyl) and three hydrazines, hydrazine itself, phenylhydrazine and thiosemicarbazide. Several products were identified, and some reaction paths established thanks to the evolution of 1H and 13C NMR spectra with time. Theoretical calculations on energies and chemical shifts were of paramount importance to ascertain the structure of some products. For important steps, the transition states were calculated while IRCs proved necessary to find some unexpected intermediates.ELSEVIER202420242021info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10578/38427reponame:RUIdeRA. Repositorio Institucional de la UCLMinstname:Universidad de Castilla-La ManchaInglésPGC2018- 094644-B-C22 and CTQ2017-84825-R, P2018/EMT-4329 AIRTEC-CM, SBPLY/17/180501/000189)info:eu-repo/semantics/embargoedAccessoai:ruidera.uclm.es:10578/384272026-05-27T07:36:41Z
dc.title.none.fl_str_mv The mechanism of the reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford 2-pyrazolines (4,5-dihydro-1H-pyrazoles): experimental and theoretical results
title The mechanism of the reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford 2-pyrazolines (4,5-dihydro-1H-pyrazoles): experimental and theoretical results
spellingShingle The mechanism of the reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford 2-pyrazolines (4,5-dihydro-1H-pyrazoles): experimental and theoretical results
Hoz Ayuso, Antonio de la
Pyrazolines, Dihydropyrazoles, Hydrazones, IRC, GIAO, NMR
title_short The mechanism of the reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford 2-pyrazolines (4,5-dihydro-1H-pyrazoles): experimental and theoretical results
title_full The mechanism of the reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford 2-pyrazolines (4,5-dihydro-1H-pyrazoles): experimental and theoretical results
title_fullStr The mechanism of the reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford 2-pyrazolines (4,5-dihydro-1H-pyrazoles): experimental and theoretical results
title_full_unstemmed The mechanism of the reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford 2-pyrazolines (4,5-dihydro-1H-pyrazoles): experimental and theoretical results
title_sort The mechanism of the reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford 2-pyrazolines (4,5-dihydro-1H-pyrazoles): experimental and theoretical results
dc.creator.none.fl_str_mv Hoz Ayuso, Antonio de la
Alkorta, Ibón
Elguero, José
author Hoz Ayuso, Antonio de la
author_facet Hoz Ayuso, Antonio de la
Alkorta, Ibón
Elguero, José
author_role author
author2 Alkorta, Ibón
Elguero, José
author2_role author
author
dc.subject.none.fl_str_mv Pyrazolines, Dihydropyrazoles, Hydrazones, IRC, GIAO, NMR
topic Pyrazolines, Dihydropyrazoles, Hydrazones, IRC, GIAO, NMR
description The reaction of hydrazines with a,b-unsaturated carbonyl compounds to afford 2-pyrazolines was studied using a dissymmetric chalcone (phenyl/p-tolyl) and three hydrazines, hydrazine itself, phenylhydrazine and thiosemicarbazide. Several products were identified, and some reaction paths established thanks to the evolution of 1H and 13C NMR spectra with time. Theoretical calculations on energies and chemical shifts were of paramount importance to ascertain the structure of some products. For important steps, the transition states were calculated while IRCs proved necessary to find some unexpected intermediates.
publishDate 2021
dc.date.none.fl_str_mv 2021
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/10578/38427
url https://hdl.handle.net/10578/38427
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv PGC2018- 094644-B-C22 and CTQ2017-84825-R, P2018/EMT-4329 AIRTEC-CM, SBPLY/17/180501/000189)
dc.rights.none.fl_str_mv info:eu-repo/semantics/embargoedAccess
eu_rights_str_mv embargoedAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv ELSEVIER
publisher.none.fl_str_mv ELSEVIER
dc.source.none.fl_str_mv reponame:RUIdeRA. Repositorio Institucional de la UCLM
instname:Universidad de Castilla-La Mancha
instname_str Universidad de Castilla-La Mancha
reponame_str RUIdeRA. Repositorio Institucional de la UCLM
collection RUIdeRA. Repositorio Institucional de la UCLM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,228081

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