Determination of the pKa of hydroxy-benzophenones in ethanol-water mixtures. Solvent effects

Autores
Castro, Gabriela Tatiana; Giordano, Oscar Santiago; Blanco, Sonia Encarnacion
Año de publicación
2003
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Benzophenones are compounds of great importance due to their biological and physicochemical properties. The purpose of the present work was to determine by a UV-Visible spectroscopic method, the pKa of 4(OH)benzophenone, 2(OH)benzophenone and 2(OH),4(CH3O)benzophenone in ethanol-water solutions, varying solvent permittivity in the interval 61-72, at constant ionic strength (0.050) and temperature (25.0 ± 0.1 °C). The pKa values of the compounds increase when the polarity-polarizability and solvation abilities of the reaction medium decrease. Correlations were established between the pKa values and solvation parameters of the solvents, such as the relative permittivity, the α parameter of Taft the solvatochromatic polarity-polarizability parameter π* and the parameter Acity. Excellent linear equations were obtained from which pKa values were determines in pure water. The structures of all the chemical species involved in the acid-base dissociation equilibria studied were calculated at the RHF/6-31G(d) level of theory, in ethanol and water. Considering the theoretical pKa values, the conclusions obtained match our experimental determinations.
Fil: Castro, Gabriela Tatiana. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Giordano, Oscar Santiago. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Blanco, Sonia Encarnacion. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Materia
AB INITIO CALCULATIONS
HYDROXY-BENZOPHENONES
PKA
SOLVATION PARAMETERS
SOLVENT EFFECTS
STRUCTURE
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:11336/159463
Acceder
id CONICETDig_e9d5c046c9afad106afb699b90a525db
oai_identifier_str oai:ri.conicet.gov.ar:11336/159463
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Determination of the pKa of hydroxy-benzophenones in ethanol-water mixtures. Solvent effectsCastro, Gabriela TatianaGiordano, Oscar SantiagoBlanco, Sonia EncarnacionAB INITIO CALCULATIONSHYDROXY-BENZOPHENONESPKASOLVATION PARAMETERSSOLVENT EFFECTSSTRUCTUREhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Benzophenones are compounds of great importance due to their biological and physicochemical properties. The purpose of the present work was to determine by a UV-Visible spectroscopic method, the pKa of 4(OH)benzophenone, 2(OH)benzophenone and 2(OH),4(CH3O)benzophenone in ethanol-water solutions, varying solvent permittivity in the interval 61-72, at constant ionic strength (0.050) and temperature (25.0 ± 0.1 °C). The pKa values of the compounds increase when the polarity-polarizability and solvation abilities of the reaction medium decrease. Correlations were established between the pKa values and solvation parameters of the solvents, such as the relative permittivity, the α parameter of Taft the solvatochromatic polarity-polarizability parameter π* and the parameter Acity. Excellent linear equations were obtained from which pKa values were determines in pure water. The structures of all the chemical species involved in the acid-base dissociation equilibria studied were calculated at the RHF/6-31G(d) level of theory, in ethanol and water. Considering the theoretical pKa values, the conclusions obtained match our experimental determinations.Fil: Castro, Gabriela Tatiana. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; ArgentinaFil: Giordano, Oscar Santiago. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Blanco, Sonia Encarnacion. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaElsevier Science2003-05-30info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/159463Castro, Gabriela Tatiana; Giordano, Oscar Santiago; Blanco, Sonia Encarnacion; Determination of the pKa of hydroxy-benzophenones in ethanol-water mixtures. Solvent effects; Elsevier Science; Journal of Molecular Structure Theochem; 626; 1-3; 30-5-2003; 167-1780166-1280CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/S0166-1280(03)00079-4info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0166128003000794info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:37:47Zoai:ri.conicet.gov.ar:11336/159463instacron: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 09:37:48.252CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Determination of the pKa of hydroxy-benzophenones in ethanol-water mixtures. Solvent effects
title Determination of the pKa of hydroxy-benzophenones in ethanol-water mixtures. Solvent effects
spellingShingle Determination of the pKa of hydroxy-benzophenones in ethanol-water mixtures. Solvent effects
Castro, Gabriela Tatiana
AB INITIO CALCULATIONS
HYDROXY-BENZOPHENONES
PKA
SOLVATION PARAMETERS
SOLVENT EFFECTS
STRUCTURE
title_short Determination of the pKa of hydroxy-benzophenones in ethanol-water mixtures. Solvent effects
title_full Determination of the pKa of hydroxy-benzophenones in ethanol-water mixtures. Solvent effects
title_fullStr Determination of the pKa of hydroxy-benzophenones in ethanol-water mixtures. Solvent effects
title_full_unstemmed Determination of the pKa of hydroxy-benzophenones in ethanol-water mixtures. Solvent effects
title_sort Determination of the pKa of hydroxy-benzophenones in ethanol-water mixtures. Solvent effects
dc.creator.none.fl_str_mv Castro, Gabriela Tatiana
Giordano, Oscar Santiago
Blanco, Sonia Encarnacion
author Castro, Gabriela Tatiana
author_facet Castro, Gabriela Tatiana
Giordano, Oscar Santiago
Blanco, Sonia Encarnacion
author_role author
author2 Giordano, Oscar Santiago
Blanco, Sonia Encarnacion
author2_role author
author
dc.subject.none.fl_str_mv AB INITIO CALCULATIONS
HYDROXY-BENZOPHENONES
PKA
SOLVATION PARAMETERS
SOLVENT EFFECTS
STRUCTURE
topic AB INITIO CALCULATIONS
HYDROXY-BENZOPHENONES
PKA
SOLVATION PARAMETERS
SOLVENT EFFECTS
STRUCTURE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Benzophenones are compounds of great importance due to their biological and physicochemical properties. The purpose of the present work was to determine by a UV-Visible spectroscopic method, the pKa of 4(OH)benzophenone, 2(OH)benzophenone and 2(OH),4(CH3O)benzophenone in ethanol-water solutions, varying solvent permittivity in the interval 61-72, at constant ionic strength (0.050) and temperature (25.0 ± 0.1 °C). The pKa values of the compounds increase when the polarity-polarizability and solvation abilities of the reaction medium decrease. Correlations were established between the pKa values and solvation parameters of the solvents, such as the relative permittivity, the α parameter of Taft the solvatochromatic polarity-polarizability parameter π* and the parameter Acity. Excellent linear equations were obtained from which pKa values were determines in pure water. The structures of all the chemical species involved in the acid-base dissociation equilibria studied were calculated at the RHF/6-31G(d) level of theory, in ethanol and water. Considering the theoretical pKa values, the conclusions obtained match our experimental determinations.
Fil: Castro, Gabriela Tatiana. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Giordano, Oscar Santiago. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Blanco, Sonia Encarnacion. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
description Benzophenones are compounds of great importance due to their biological and physicochemical properties. The purpose of the present work was to determine by a UV-Visible spectroscopic method, the pKa of 4(OH)benzophenone, 2(OH)benzophenone and 2(OH),4(CH3O)benzophenone in ethanol-water solutions, varying solvent permittivity in the interval 61-72, at constant ionic strength (0.050) and temperature (25.0 ± 0.1 °C). The pKa values of the compounds increase when the polarity-polarizability and solvation abilities of the reaction medium decrease. Correlations were established between the pKa values and solvation parameters of the solvents, such as the relative permittivity, the α parameter of Taft the solvatochromatic polarity-polarizability parameter π* and the parameter Acity. Excellent linear equations were obtained from which pKa values were determines in pure water. The structures of all the chemical species involved in the acid-base dissociation equilibria studied were calculated at the RHF/6-31G(d) level of theory, in ethanol and water. Considering the theoretical pKa values, the conclusions obtained match our experimental determinations.
publishDate 2003
dc.date.none.fl_str_mv 2003-05-30
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/11336/159463
Castro, Gabriela Tatiana; Giordano, Oscar Santiago; Blanco, Sonia Encarnacion; Determination of the pKa of hydroxy-benzophenones in ethanol-water mixtures. Solvent effects; Elsevier Science; Journal of Molecular Structure Theochem; 626; 1-3; 30-5-2003; 167-178
0166-1280
CONICET Digital
CONICET
url http://hdl.handle.net/11336/159463
identifier_str_mv Castro, Gabriela Tatiana; Giordano, Oscar Santiago; Blanco, Sonia Encarnacion; Determination of the pKa of hydroxy-benzophenones in ethanol-water mixtures. Solvent effects; Elsevier Science; Journal of Molecular Structure Theochem; 626; 1-3; 30-5-2003; 167-178
0166-1280
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/S0166-1280(03)00079-4
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0166128003000794
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 Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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_ 1844613192758591488
score 13.070432

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