Betanidin pKa prediction using DFT methods

Autores
Rodriguez, Sergio A.; Baumgartner, Maria Teresa del V.
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Betalains can be used in food, drugs, and cosmetic industries and have shown their bioactive potential. These properties are strongly influenced by pH and other physicochemical conditions. The pKa values for the polyprotic Betanidin (Bd) molecule are unknown, and they are crucial to elucidate the oxidation mechanism in which its pigment is involved. In the present study, the values of pKa for all protic groups of Bd were analyzed using five hybrid density functionals (B3LYP, B3PW91, ωB97XD, PBE0, and M06-2X), five basis sets (6-31+G(d), 6-31+G(d,p), 6-31++G(d,p), 6-311+G(d,p), and 6-311++G(d,p)) and the solvation model based on density (SMD) implicit solvation model. Moreover, one and three explicit water molecules were added to improve the solvation free energy values. Furthermore, the values of pKa of betanin, betalamic acid, and cyclo-dihydroxyphenylalanine (DOPA) were studied. Based on these analyses, we propose the acid-base behavior of Bd in water and develop new tools to understand their chemical reactivity.
Fil: Rodriguez, Sergio A.. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina
Fil: Baumgartner, Maria Teresa del V.. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. 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
Materia
Polyprotic molecule
PKa values
Solvation models
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:11336/144362
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Betanidin pKa prediction using DFT methodsRodriguez, Sergio A.Baumgartner, Maria Teresa del V.Polyprotic moleculePKa valuesSolvation modelshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Betalains can be used in food, drugs, and cosmetic industries and have shown their bioactive potential. These properties are strongly influenced by pH and other physicochemical conditions. The pKa values for the polyprotic Betanidin (Bd) molecule are unknown, and they are crucial to elucidate the oxidation mechanism in which its pigment is involved. In the present study, the values of pKa for all protic groups of Bd were analyzed using five hybrid density functionals (B3LYP, B3PW91, ωB97XD, PBE0, and M06-2X), five basis sets (6-31+G(d), 6-31+G(d,p), 6-31++G(d,p), 6-311+G(d,p), and 6-311++G(d,p)) and the solvation model based on density (SMD) implicit solvation model. Moreover, one and three explicit water molecules were added to improve the solvation free energy values. Furthermore, the values of pKa of betanin, betalamic acid, and cyclo-dihydroxyphenylalanine (DOPA) were studied. Based on these analyses, we propose the acid-base behavior of Bd in water and develop new tools to understand their chemical reactivity.Fil: Rodriguez, Sergio A.. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; ArgentinaFil: Baumgartner, Maria Teresa del V.. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. 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; ArgentinaAmerican Chemical Society2020-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/144362Rodriguez, Sergio A.; Baumgartner, Maria Teresa del V.; Betanidin pKa prediction using DFT methods; American Chemical Society; ACS Omega; 5; 23; 6-2020; 13751-137592470-1343CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acsomega.0c00904info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acsomega.0c00904info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:26:56Zoai:ri.conicet.gov.ar:11336/144362instacron: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:34982025-10-22 11:26:56.334CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Betanidin pKa prediction using DFT methods
title Betanidin pKa prediction using DFT methods
spellingShingle Betanidin pKa prediction using DFT methods
Rodriguez, Sergio A.
Polyprotic molecule
PKa values
Solvation models
title_short Betanidin pKa prediction using DFT methods
title_full Betanidin pKa prediction using DFT methods
title_fullStr Betanidin pKa prediction using DFT methods
title_full_unstemmed Betanidin pKa prediction using DFT methods
title_sort Betanidin pKa prediction using DFT methods
dc.creator.none.fl_str_mv Rodriguez, Sergio A.
Baumgartner, Maria Teresa del V.
author Rodriguez, Sergio A.
author_facet Rodriguez, Sergio A.
Baumgartner, Maria Teresa del V.
author_role author
author2 Baumgartner, Maria Teresa del V.
author2_role author
dc.subject.none.fl_str_mv Polyprotic molecule
PKa values
Solvation models
topic Polyprotic molecule
PKa values
Solvation models
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Betalains can be used in food, drugs, and cosmetic industries and have shown their bioactive potential. These properties are strongly influenced by pH and other physicochemical conditions. The pKa values for the polyprotic Betanidin (Bd) molecule are unknown, and they are crucial to elucidate the oxidation mechanism in which its pigment is involved. In the present study, the values of pKa for all protic groups of Bd were analyzed using five hybrid density functionals (B3LYP, B3PW91, ωB97XD, PBE0, and M06-2X), five basis sets (6-31+G(d), 6-31+G(d,p), 6-31++G(d,p), 6-311+G(d,p), and 6-311++G(d,p)) and the solvation model based on density (SMD) implicit solvation model. Moreover, one and three explicit water molecules were added to improve the solvation free energy values. Furthermore, the values of pKa of betanin, betalamic acid, and cyclo-dihydroxyphenylalanine (DOPA) were studied. Based on these analyses, we propose the acid-base behavior of Bd in water and develop new tools to understand their chemical reactivity.
Fil: Rodriguez, Sergio A.. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina
Fil: Baumgartner, Maria Teresa del V.. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. 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
description Betalains can be used in food, drugs, and cosmetic industries and have shown their bioactive potential. These properties are strongly influenced by pH and other physicochemical conditions. The pKa values for the polyprotic Betanidin (Bd) molecule are unknown, and they are crucial to elucidate the oxidation mechanism in which its pigment is involved. In the present study, the values of pKa for all protic groups of Bd were analyzed using five hybrid density functionals (B3LYP, B3PW91, ωB97XD, PBE0, and M06-2X), five basis sets (6-31+G(d), 6-31+G(d,p), 6-31++G(d,p), 6-311+G(d,p), and 6-311++G(d,p)) and the solvation model based on density (SMD) implicit solvation model. Moreover, one and three explicit water molecules were added to improve the solvation free energy values. Furthermore, the values of pKa of betanin, betalamic acid, and cyclo-dihydroxyphenylalanine (DOPA) were studied. Based on these analyses, we propose the acid-base behavior of Bd in water and develop new tools to understand their chemical reactivity.
publishDate 2020
dc.date.none.fl_str_mv 2020-06
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/11336/144362
Rodriguez, Sergio A.; Baumgartner, Maria Teresa del V.; Betanidin pKa prediction using DFT methods; American Chemical Society; ACS Omega; 5; 23; 6-2020; 13751-13759
2470-1343
CONICET Digital
CONICET
url http://hdl.handle.net/11336/144362
identifier_str_mv Rodriguez, Sergio A.; Baumgartner, Maria Teresa del V.; Betanidin pKa prediction using DFT methods; American Chemical Society; ACS Omega; 5; 23; 6-2020; 13751-13759
2470-1343
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/acsomega.0c00904
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acsomega.0c00904
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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
_version_ 1846781832812560384
score 12.982451

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