Structural study of some unsaturated malononitriles using mass spectrometry and theoretical models

Autores
Garofalo, Federico Mariano; Gastaca, Belén; Albesa, Alberto Gustavo; Furlong, Jorge Javier Pedro; Allegretti, Patricia Ercilia; Giussi, Juan Martín
Año de publicación
2023
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The study of tautomerism has gained relevance in the scientific community because several cellular processes occur through different tautomeric forms of certain compounds. The percentage of each tautomer in compounds with tautomerism capability depends on numerous factors, such as temperature and solvent polarity, among others; and, by changing the external conditions, equilibrium displacement can be established very quickly. This manuscript deals with nitrile–ketenimine tautomerism in some unsaturated malononitriles. This kind of compounds with two nitrile groups conjugated to a double bound is able to rearrange accessible hydrogens and provide new and complex structures of different functionalities. The authors' motivation for investigating these compounds lies in understanding their tautomeric behavior in solution and gas phases and to predict reaction deportment to then account for the final products obtained. Four unsaturated malononitriles were synthesized to study the substituent effect on equilibrium displacement. Characterization was performed using nuclear magnetic resonance (NMR) and tautomeric equilibrium in gas phase was evaluated by mass spectrometry. Correlation with theoretical calculations was carried out in order to comprehend the system behavior.
Centro de Estudios de Compuestos Orgánicos
Comisión de Investigaciones Científicas de la provincia de Buenos Aires
Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas
Materia
Química
DFT calculations
nitrile-ketenimine tautomerism
NMR and mass spectrometry
unsaturated malononitriles
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by-nc-sa/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/166618
Acceder
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network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling Structural study of some unsaturated malononitriles using mass spectrometry and theoretical modelsGarofalo, Federico MarianoGastaca, BelénAlbesa, Alberto GustavoFurlong, Jorge Javier PedroAllegretti, Patricia ErciliaGiussi, Juan MartínQuímicaDFT calculationsnitrile-ketenimine tautomerismNMR and mass spectrometryunsaturated malononitrilesThe study of tautomerism has gained relevance in the scientific community because several cellular processes occur through different tautomeric forms of certain compounds. The percentage of each tautomer in compounds with tautomerism capability depends on numerous factors, such as temperature and solvent polarity, among others; and, by changing the external conditions, equilibrium displacement can be established very quickly. This manuscript deals with nitrile–ketenimine tautomerism in some unsaturated malononitriles. This kind of compounds with two nitrile groups conjugated to a double bound is able to rearrange accessible hydrogens and provide new and complex structures of different functionalities. The authors' motivation for investigating these compounds lies in understanding their tautomeric behavior in solution and gas phases and to predict reaction deportment to then account for the final products obtained. Four unsaturated malononitriles were synthesized to study the substituent effect on equilibrium displacement. Characterization was performed using nuclear magnetic resonance (NMR) and tautomeric equilibrium in gas phase was evaluated by mass spectrometry. Correlation with theoretical calculations was carried out in order to comprehend the system behavior.Centro de Estudios de Compuestos OrgánicosComisión de Investigaciones Científicas de la provincia de Buenos AiresInstituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas2023-04-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfhttp://sedici.unlp.edu.ar/handle/10915/166618enginfo:eu-repo/semantics/altIdentifier/issn/1099-1395info:eu-repo/semantics/altIdentifier/doi/10.1002/poc.4511info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-sa/4.0/Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-10-15T11:36:10Zoai:sedici.unlp.edu.ar:10915/166618Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-10-15 11:36:10.869SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Structural study of some unsaturated malononitriles using mass spectrometry and theoretical models
title Structural study of some unsaturated malononitriles using mass spectrometry and theoretical models
spellingShingle Structural study of some unsaturated malononitriles using mass spectrometry and theoretical models
Garofalo, Federico Mariano
Química
DFT calculations
nitrile-ketenimine tautomerism
NMR and mass spectrometry
unsaturated malononitriles
title_short Structural study of some unsaturated malononitriles using mass spectrometry and theoretical models
title_full Structural study of some unsaturated malononitriles using mass spectrometry and theoretical models
title_fullStr Structural study of some unsaturated malononitriles using mass spectrometry and theoretical models
title_full_unstemmed Structural study of some unsaturated malononitriles using mass spectrometry and theoretical models
title_sort Structural study of some unsaturated malononitriles using mass spectrometry and theoretical models
dc.creator.none.fl_str_mv Garofalo, Federico Mariano
Gastaca, Belén
Albesa, Alberto Gustavo
Furlong, Jorge Javier Pedro
Allegretti, Patricia Ercilia
Giussi, Juan Martín
author Garofalo, Federico Mariano
author_facet Garofalo, Federico Mariano
Gastaca, Belén
Albesa, Alberto Gustavo
Furlong, Jorge Javier Pedro
Allegretti, Patricia Ercilia
Giussi, Juan Martín
author_role author
author2 Gastaca, Belén
Albesa, Alberto Gustavo
Furlong, Jorge Javier Pedro
Allegretti, Patricia Ercilia
Giussi, Juan Martín
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Química
DFT calculations
nitrile-ketenimine tautomerism
NMR and mass spectrometry
unsaturated malononitriles
topic Química
DFT calculations
nitrile-ketenimine tautomerism
NMR and mass spectrometry
unsaturated malononitriles
dc.description.none.fl_txt_mv The study of tautomerism has gained relevance in the scientific community because several cellular processes occur through different tautomeric forms of certain compounds. The percentage of each tautomer in compounds with tautomerism capability depends on numerous factors, such as temperature and solvent polarity, among others; and, by changing the external conditions, equilibrium displacement can be established very quickly. This manuscript deals with nitrile–ketenimine tautomerism in some unsaturated malononitriles. This kind of compounds with two nitrile groups conjugated to a double bound is able to rearrange accessible hydrogens and provide new and complex structures of different functionalities. The authors' motivation for investigating these compounds lies in understanding their tautomeric behavior in solution and gas phases and to predict reaction deportment to then account for the final products obtained. Four unsaturated malononitriles were synthesized to study the substituent effect on equilibrium displacement. Characterization was performed using nuclear magnetic resonance (NMR) and tautomeric equilibrium in gas phase was evaluated by mass spectrometry. Correlation with theoretical calculations was carried out in order to comprehend the system behavior.
Centro de Estudios de Compuestos Orgánicos
Comisión de Investigaciones Científicas de la provincia de Buenos Aires
Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas
description The study of tautomerism has gained relevance in the scientific community because several cellular processes occur through different tautomeric forms of certain compounds. The percentage of each tautomer in compounds with tautomerism capability depends on numerous factors, such as temperature and solvent polarity, among others; and, by changing the external conditions, equilibrium displacement can be established very quickly. This manuscript deals with nitrile–ketenimine tautomerism in some unsaturated malononitriles. This kind of compounds with two nitrile groups conjugated to a double bound is able to rearrange accessible hydrogens and provide new and complex structures of different functionalities. The authors' motivation for investigating these compounds lies in understanding their tautomeric behavior in solution and gas phases and to predict reaction deportment to then account for the final products obtained. Four unsaturated malononitriles were synthesized to study the substituent effect on equilibrium displacement. Characterization was performed using nuclear magnetic resonance (NMR) and tautomeric equilibrium in gas phase was evaluated by mass spectrometry. Correlation with theoretical calculations was carried out in order to comprehend the system behavior.
publishDate 2023
dc.date.none.fl_str_mv 2023-04-06
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
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://sedici.unlp.edu.ar/handle/10915/166618
url http://sedici.unlp.edu.ar/handle/10915/166618
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/1099-1395
info:eu-repo/semantics/altIdentifier/doi/10.1002/poc.4511
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-sa/4.0/
Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-sa/4.0/
Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
instacron:UNLP
reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
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score 13.22299

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