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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/144362
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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 Técnicas2025-09-29T09:57:39Zoai: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:34982025-09-29 09:57:39.481CONICET 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 |
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1844613723221655552 |
score |
13.070432 |