Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines

Autores
Havlík, Martin; Navrátilová, Tereza; Drozdová, Michaela; Tatar, Ameneh; Lanza Castronuovo, Priscila Ailin; Dusso, Diego; Moyano, Elizabeth Laura; Chesta, Carlos Alberto; Vera, Domingo Mariano Adolfo; Dolenský, Bohumil
Año de publicación
2023
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The reactions of 2-naphthylamine and methyl 6-amino-2-naphthoate with formalin and paraformaldehyde were studied experimentally, spectrally, and by quantum chemical calculations. It was found that neither the corresponding aminals nor imines were formed under the described conditions but could be prepared and spectrally characterized at least in situ under modified conditions. Several of the previously undescribed intermediates and by-products were isolated or at least spectrally characterized. First principle density functional theory (DFT) calculations were performed to shed light on the key aspects of the thermochemistry of decomposition and further condensation of the corresponding aminals and imines. The calculations also revealed that the electrophilicity of methanal was significantly greater than that of ordinary oxo-compounds, except for perfluorinated ones. In summary, methanal was not behaving as the simplest aldehyde but as a very electron-deficient oxo-compound.
Fil: Havlík, Martin. University Of Chemistry And Technology, Prague; República Checa
Fil: Navrátilová, Tereza. University Of Chemistry And Technology, Prague; República Checa
Fil: Drozdová, Michaela. University Of Chemistry And Technology, Prague; República Checa
Fil: Tatar, Ameneh. University Of Chemistry And Technology, Prague; República Checa
Fil: Lanza Castronuovo, Priscila Ailin. Universidad Nacional de Mar del Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones En Biodiversidad y Biotecnología. Grupo de Investigación en Química Analítica y Modelado Molecular; Argentina
Fil: Dusso, Diego. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones En Biodiversidad y Biotecnología. Grupo de Investigación en Química Analítica y Modelado Molecular; Argentina. Universidad Nacional de Mar del Plata; Argentina
Fil: Moyano, Elizabeth Laura. Universidad Nacional de Córdoba; Argentina
Fil: Chesta, Carlos Alberto. Universidad Nacional de Córdoba; Argentina
Fil: Vera, Domingo Mariano Adolfo. Universidad Nacional de Río Cuarto; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones En Biodiversidad y Biotecnología. Grupo de Investigación en Química Analítica y Modelado Molecular; Argentina
Fil: Dolenský, Bohumil. Universidad Nacional de Mar del Plata; Argentina
Materia
DFT
MECHANISMS
METHANAL
NAPHTHYLAMINE
QUINAZOLINE
SPIRO-TRÖGER’S BASE
TRÖGER’S BASE
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/230085
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/230085
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-NaphthylaminesHavlík, MartinNavrátilová, TerezaDrozdová, MichaelaTatar, AmenehLanza Castronuovo, Priscila AilinDusso, DiegoMoyano, Elizabeth LauraChesta, Carlos AlbertoVera, Domingo Mariano AdolfoDolenský, BohumilDFTMECHANISMSMETHANALNAPHTHYLAMINEQUINAZOLINESPIRO-TRÖGER’S BASETRÖGER’S BASEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The reactions of 2-naphthylamine and methyl 6-amino-2-naphthoate with formalin and paraformaldehyde were studied experimentally, spectrally, and by quantum chemical calculations. It was found that neither the corresponding aminals nor imines were formed under the described conditions but could be prepared and spectrally characterized at least in situ under modified conditions. Several of the previously undescribed intermediates and by-products were isolated or at least spectrally characterized. First principle density functional theory (DFT) calculations were performed to shed light on the key aspects of the thermochemistry of decomposition and further condensation of the corresponding aminals and imines. The calculations also revealed that the electrophilicity of methanal was significantly greater than that of ordinary oxo-compounds, except for perfluorinated ones. In summary, methanal was not behaving as the simplest aldehyde but as a very electron-deficient oxo-compound.Fil: Havlík, Martin. University Of Chemistry And Technology, Prague; República ChecaFil: Navrátilová, Tereza. University Of Chemistry And Technology, Prague; República ChecaFil: Drozdová, Michaela. University Of Chemistry And Technology, Prague; República ChecaFil: Tatar, Ameneh. University Of Chemistry And Technology, Prague; República ChecaFil: Lanza Castronuovo, Priscila Ailin. Universidad Nacional de Mar del Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones En Biodiversidad y Biotecnología. Grupo de Investigación en Química Analítica y Modelado Molecular; ArgentinaFil: Dusso, Diego. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones En Biodiversidad y Biotecnología. Grupo de Investigación en Química Analítica y Modelado Molecular; Argentina. Universidad Nacional de Mar del Plata; ArgentinaFil: Moyano, Elizabeth Laura. Universidad Nacional de Córdoba; ArgentinaFil: Chesta, Carlos Alberto. Universidad Nacional de Córdoba; ArgentinaFil: Vera, Domingo Mariano Adolfo. Universidad Nacional de Río Cuarto; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones En Biodiversidad y Biotecnología. Grupo de Investigación en Química Analítica y Modelado Molecular; ArgentinaFil: Dolenský, Bohumil. Universidad Nacional de Mar del Plata; ArgentinaMolecular Diversity Preservation International2023-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/230085Havlík, Martin; Navrátilová, Tereza; Drozdová, Michaela; Tatar, Ameneh; Lanza Castronuovo, Priscila Ailin; et al.; Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines; Molecular Diversity Preservation International; Molecules; 28; 4; 2-2023; 1549-15491420-3049CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/28/4/1549info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules28041549info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:02:06Zoai:ri.conicet.gov.ar:11336/230085instacron: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:34982025-09-10 13:02:06.687CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines
title Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines
spellingShingle Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines
Havlík, Martin
DFT
MECHANISMS
METHANAL
NAPHTHYLAMINE
QUINAZOLINE
SPIRO-TRÖGER’S BASE
TRÖGER’S BASE
title_short Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines
title_full Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines
title_fullStr Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines
title_full_unstemmed Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines
title_sort Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines
dc.creator.none.fl_str_mv Havlík, Martin
Navrátilová, Tereza
Drozdová, Michaela
Tatar, Ameneh
Lanza Castronuovo, Priscila Ailin
Dusso, Diego
Moyano, Elizabeth Laura
Chesta, Carlos Alberto
Vera, Domingo Mariano Adolfo
Dolenský, Bohumil
author Havlík, Martin
author_facet Havlík, Martin
Navrátilová, Tereza
Drozdová, Michaela
Tatar, Ameneh
Lanza Castronuovo, Priscila Ailin
Dusso, Diego
Moyano, Elizabeth Laura
Chesta, Carlos Alberto
Vera, Domingo Mariano Adolfo
Dolenský, Bohumil
author_role author
author2 Navrátilová, Tereza
Drozdová, Michaela
Tatar, Ameneh
Lanza Castronuovo, Priscila Ailin
Dusso, Diego
Moyano, Elizabeth Laura
Chesta, Carlos Alberto
Vera, Domingo Mariano Adolfo
Dolenský, Bohumil
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv DFT
MECHANISMS
METHANAL
NAPHTHYLAMINE
QUINAZOLINE
SPIRO-TRÖGER’S BASE
TRÖGER’S BASE
topic DFT
MECHANISMS
METHANAL
NAPHTHYLAMINE
QUINAZOLINE
SPIRO-TRÖGER’S BASE
TRÖGER’S BASE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The reactions of 2-naphthylamine and methyl 6-amino-2-naphthoate with formalin and paraformaldehyde were studied experimentally, spectrally, and by quantum chemical calculations. It was found that neither the corresponding aminals nor imines were formed under the described conditions but could be prepared and spectrally characterized at least in situ under modified conditions. Several of the previously undescribed intermediates and by-products were isolated or at least spectrally characterized. First principle density functional theory (DFT) calculations were performed to shed light on the key aspects of the thermochemistry of decomposition and further condensation of the corresponding aminals and imines. The calculations also revealed that the electrophilicity of methanal was significantly greater than that of ordinary oxo-compounds, except for perfluorinated ones. In summary, methanal was not behaving as the simplest aldehyde but as a very electron-deficient oxo-compound.
Fil: Havlík, Martin. University Of Chemistry And Technology, Prague; República Checa
Fil: Navrátilová, Tereza. University Of Chemistry And Technology, Prague; República Checa
Fil: Drozdová, Michaela. University Of Chemistry And Technology, Prague; República Checa
Fil: Tatar, Ameneh. University Of Chemistry And Technology, Prague; República Checa
Fil: Lanza Castronuovo, Priscila Ailin. Universidad Nacional de Mar del Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones En Biodiversidad y Biotecnología. Grupo de Investigación en Química Analítica y Modelado Molecular; Argentina
Fil: Dusso, Diego. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones En Biodiversidad y Biotecnología. Grupo de Investigación en Química Analítica y Modelado Molecular; Argentina. Universidad Nacional de Mar del Plata; Argentina
Fil: Moyano, Elizabeth Laura. Universidad Nacional de Córdoba; Argentina
Fil: Chesta, Carlos Alberto. Universidad Nacional de Córdoba; Argentina
Fil: Vera, Domingo Mariano Adolfo. Universidad Nacional de Río Cuarto; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones En Biodiversidad y Biotecnología. Grupo de Investigación en Química Analítica y Modelado Molecular; Argentina
Fil: Dolenský, Bohumil. Universidad Nacional de Mar del Plata; Argentina
description The reactions of 2-naphthylamine and methyl 6-amino-2-naphthoate with formalin and paraformaldehyde were studied experimentally, spectrally, and by quantum chemical calculations. It was found that neither the corresponding aminals nor imines were formed under the described conditions but could be prepared and spectrally characterized at least in situ under modified conditions. Several of the previously undescribed intermediates and by-products were isolated or at least spectrally characterized. First principle density functional theory (DFT) calculations were performed to shed light on the key aspects of the thermochemistry of decomposition and further condensation of the corresponding aminals and imines. The calculations also revealed that the electrophilicity of methanal was significantly greater than that of ordinary oxo-compounds, except for perfluorinated ones. In summary, methanal was not behaving as the simplest aldehyde but as a very electron-deficient oxo-compound.
publishDate 2023
dc.date.none.fl_str_mv 2023-02
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/11336/230085
Havlík, Martin; Navrátilová, Tereza; Drozdová, Michaela; Tatar, Ameneh; Lanza Castronuovo, Priscila Ailin; et al.; Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines; Molecular Diversity Preservation International; Molecules; 28; 4; 2-2023; 1549-1549
1420-3049
CONICET Digital
CONICET
url http://hdl.handle.net/11336/230085
identifier_str_mv Havlík, Martin; Navrátilová, Tereza; Drozdová, Michaela; Tatar, Ameneh; Lanza Castronuovo, Priscila Ailin; et al.; Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines; Molecular Diversity Preservation International; Molecules; 28; 4; 2-2023; 1549-1549
1420-3049
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.mdpi.com/1420-3049/28/4/1549
info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules28041549
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
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 12.993085

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