Effect of carboxyl and carboxamide substituent groups on fluorinated pyrazine species with antitubercular activities

Autores
Iramain, Maximiliano Alberto; Brandan, Silvia Antonia
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The structural, electronic, topological and vibrational properties were studied for F-pyrazine, 3-fluoropyrazine-2-carboxilic acidand 3-fluoropyrazine-2-carboxamide in gas phase by using the hybrid B3LYP/6-311++G** level of theory. Theoretically, twoconformations were found for both acid and amide species being their C2 conformations, with C symmetries, the most stable. SThe NBO study reveals the high stability of the acid species due to the two DET and DET interactions not observed in the amide LP* LP LP*species. The AIM analysis supports the high stabilities of both C2 conformers due to the halogen bonds formation where thetopological properties are higher for the acid species, in very good concordance with the higher total energy observed by NBOcalculations. The frontier orbitals predict a higher reactivity for the amide species while the descriptors evidence the highernucleophilicity and electrophilicity indexes for the acid species. On the other hand, the C2-N3 stretching mode in FP is predicted athigher wavenumbers than pyrazine while in the acid and amide species this stretching mode is predicted with partial double bondat lower wavenumbers. The tentative assignments for the acid and amide species were performed. The force constants calculatedshow strongly dependence from their geometrical parameters.
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica; Argentina
Materia
FLUORPIRAZINE
VIBRATIONAL SPECTRA
MOLECULAR STRUCTURE
DFT CALCULATIONS
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:11336/67621
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/67621
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Effect of carboxyl and carboxamide substituent groups on fluorinated pyrazine species with antitubercular activitiesIramain, Maximiliano AlbertoBrandan, Silvia AntoniaFLUORPIRAZINEVIBRATIONAL SPECTRAMOLECULAR STRUCTUREDFT CALCULATIONShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The structural, electronic, topological and vibrational properties were studied for F-pyrazine, 3-fluoropyrazine-2-carboxilic acidand 3-fluoropyrazine-2-carboxamide in gas phase by using the hybrid B3LYP/6-311++G** level of theory. Theoretically, twoconformations were found for both acid and amide species being their C2 conformations, with C symmetries, the most stable. SThe NBO study reveals the high stability of the acid species due to the two DET and DET interactions not observed in the amide LP* LP LP*species. The AIM analysis supports the high stabilities of both C2 conformers due to the halogen bonds formation where thetopological properties are higher for the acid species, in very good concordance with the higher total energy observed by NBOcalculations. The frontier orbitals predict a higher reactivity for the amide species while the descriptors evidence the highernucleophilicity and electrophilicity indexes for the acid species. On the other hand, the C2-N3 stretching mode in FP is predicted athigher wavenumbers than pyrazine while in the acid and amide species this stretching mode is predicted with partial double bondat lower wavenumbers. The tentative assignments for the acid and amide species were performed. The force constants calculatedshow strongly dependence from their geometrical parameters.Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Brandan, Silvia Antonia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica; ArgentinaWorld Wide Journals International2017-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/67621Iramain, Maximiliano Alberto; Brandan, Silvia Antonia; Effect of carboxyl and carboxamide substituent groups on fluorinated pyrazine species with antitubercular activities; World Wide Journals International; Paripex; 6; 9; 9-2017; 613-6252250-1991CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.worldwidejournals.com/paripex/recent_issues_pdf/2017/September/September_2017_1505475542__118.pdfinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:18:25Zoai:ri.conicet.gov.ar:11336/67621instacron: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:34982025-09-29 10:18:25.657CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Effect of carboxyl and carboxamide substituent groups on fluorinated pyrazine species with antitubercular activities
title Effect of carboxyl and carboxamide substituent groups on fluorinated pyrazine species with antitubercular activities
spellingShingle Effect of carboxyl and carboxamide substituent groups on fluorinated pyrazine species with antitubercular activities
Iramain, Maximiliano Alberto
FLUORPIRAZINE
VIBRATIONAL SPECTRA
MOLECULAR STRUCTURE
DFT CALCULATIONS
title_short Effect of carboxyl and carboxamide substituent groups on fluorinated pyrazine species with antitubercular activities
title_full Effect of carboxyl and carboxamide substituent groups on fluorinated pyrazine species with antitubercular activities
title_fullStr Effect of carboxyl and carboxamide substituent groups on fluorinated pyrazine species with antitubercular activities
title_full_unstemmed Effect of carboxyl and carboxamide substituent groups on fluorinated pyrazine species with antitubercular activities
title_sort Effect of carboxyl and carboxamide substituent groups on fluorinated pyrazine species with antitubercular activities
dc.creator.none.fl_str_mv Iramain, Maximiliano Alberto
Brandan, Silvia Antonia
author Iramain, Maximiliano Alberto
author_facet Iramain, Maximiliano Alberto
Brandan, Silvia Antonia
author_role author
author2 Brandan, Silvia Antonia
author2_role author
dc.subject.none.fl_str_mv FLUORPIRAZINE
VIBRATIONAL SPECTRA
MOLECULAR STRUCTURE
DFT CALCULATIONS
topic FLUORPIRAZINE
VIBRATIONAL SPECTRA
MOLECULAR STRUCTURE
DFT CALCULATIONS
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 structural, electronic, topological and vibrational properties were studied for F-pyrazine, 3-fluoropyrazine-2-carboxilic acidand 3-fluoropyrazine-2-carboxamide in gas phase by using the hybrid B3LYP/6-311++G** level of theory. Theoretically, twoconformations were found for both acid and amide species being their C2 conformations, with C symmetries, the most stable. SThe NBO study reveals the high stability of the acid species due to the two DET and DET interactions not observed in the amide LP* LP LP*species. The AIM analysis supports the high stabilities of both C2 conformers due to the halogen bonds formation where thetopological properties are higher for the acid species, in very good concordance with the higher total energy observed by NBOcalculations. The frontier orbitals predict a higher reactivity for the amide species while the descriptors evidence the highernucleophilicity and electrophilicity indexes for the acid species. On the other hand, the C2-N3 stretching mode in FP is predicted athigher wavenumbers than pyrazine while in the acid and amide species this stretching mode is predicted with partial double bondat lower wavenumbers. The tentative assignments for the acid and amide species were performed. The force constants calculatedshow strongly dependence from their geometrical parameters.
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica; Argentina
description The structural, electronic, topological and vibrational properties were studied for F-pyrazine, 3-fluoropyrazine-2-carboxilic acidand 3-fluoropyrazine-2-carboxamide in gas phase by using the hybrid B3LYP/6-311++G** level of theory. Theoretically, twoconformations were found for both acid and amide species being their C2 conformations, with C symmetries, the most stable. SThe NBO study reveals the high stability of the acid species due to the two DET and DET interactions not observed in the amide LP* LP LP*species. The AIM analysis supports the high stabilities of both C2 conformers due to the halogen bonds formation where thetopological properties are higher for the acid species, in very good concordance with the higher total energy observed by NBOcalculations. The frontier orbitals predict a higher reactivity for the amide species while the descriptors evidence the highernucleophilicity and electrophilicity indexes for the acid species. On the other hand, the C2-N3 stretching mode in FP is predicted athigher wavenumbers than pyrazine while in the acid and amide species this stretching mode is predicted with partial double bondat lower wavenumbers. The tentative assignments for the acid and amide species were performed. The force constants calculatedshow strongly dependence from their geometrical parameters.
publishDate 2017
dc.date.none.fl_str_mv 2017-09
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/11336/67621
Iramain, Maximiliano Alberto; Brandan, Silvia Antonia; Effect of carboxyl and carboxamide substituent groups on fluorinated pyrazine species with antitubercular activities; World Wide Journals International; Paripex; 6; 9; 9-2017; 613-625
2250-1991
CONICET Digital
CONICET
url http://hdl.handle.net/11336/67621
identifier_str_mv Iramain, Maximiliano Alberto; Brandan, Silvia Antonia; Effect of carboxyl and carboxamide substituent groups on fluorinated pyrazine species with antitubercular activities; World Wide Journals International; Paripex; 6; 9; 9-2017; 613-625
2250-1991
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.worldwidejournals.com/paripex/recent_issues_pdf/2017/September/September_2017_1505475542__118.pdf
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 World Wide Journals International
publisher.none.fl_str_mv World Wide Journals 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 13.070432

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