Structure and dipole moment of catechol in hydroxylic solvents

Autores
Rudyk, Roxana Amelia; Molina, María A. A.; Gómez, María Inés; Blanco, Sonia Encarnacion; Ferretti, Ferdinando Hector
Año de publicación
2004
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Motivation. Various classes of flavonoids of great importance for medicine have a molecular structure containing a resorcinol in its A-ring whereas the B-ring is a catechol derivative. With a future view to establishing correlations between the physicochemical and biological properties of flavonoids and catechols and with the specific aim of explaining the dipole moment of catechol in water, we investigated the molecular conformations and solute-solvent interactions of catechol in ethanol, methanol and water. Method. Basis sets at two levels of theory: HF/6-31G(d,p) and B3LYP/6-31G(d,p) were used for calculations. Onsager's method was used to analyze the solvent effects on the conformers of catechol. Results. A conformational equilibrium between the two main conformers of non-solvated catechol was proposed. The total energies, dipole moments, structural molecular and reactivity parameters of the conformers and transition states involved were calculated. These theoretical magnitudes were correlated with properties of the solvating solvents. The properties of solute-solvent association complexes formed by a molecule of catechol and three molecules of water by means of intermolecular hydrogen bonds were also calculated. Conclusions. The stability of the conformer that has one intramolecular hydrogen bond increases with the hydrogen-bond donor capability and polarity of the solvents. The dipole moment of catechol in water (11.45 D) is due to the solute-solvent association complexes, which are the predominant forms of the compound in aqueous solutions.
Fil: Rudyk, Roxana Amelia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica. Cátedra de Química General.; Argentina
Fil: Molina, María A. A.. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica. Cátedra de Química General.; Argentina
Fil: Gómez, María Inés. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica. Cátedra de Química General.; 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. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química. Área de Química Física; Argentina
Fil: Ferretti, Ferdinando Hector. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química. Área de Química Física; Argentina
Materia
Catechol
Conformations
Dipole moment
Hydrogen bonding
Solvent effects
Association complexes
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:11336/138819
Acceder
id CONICETDig_85f42ff5bdfea7bec40a8d26e0779ce8
oai_identifier_str oai:ri.conicet.gov.ar:11336/138819
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Structure and dipole moment of catechol in hydroxylic solventsRudyk, Roxana AmeliaMolina, María A. A.Gómez, María InésBlanco, Sonia EncarnacionFerretti, Ferdinando HectorCatecholConformationsDipole momentHydrogen bondingSolvent effectsAssociation complexesDFT calculationshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Motivation. Various classes of flavonoids of great importance for medicine have a molecular structure containing a resorcinol in its A-ring whereas the B-ring is a catechol derivative. With a future view to establishing correlations between the physicochemical and biological properties of flavonoids and catechols and with the specific aim of explaining the dipole moment of catechol in water, we investigated the molecular conformations and solute-solvent interactions of catechol in ethanol, methanol and water. Method. Basis sets at two levels of theory: HF/6-31G(d,p) and B3LYP/6-31G(d,p) were used for calculations. Onsager's method was used to analyze the solvent effects on the conformers of catechol. Results. A conformational equilibrium between the two main conformers of non-solvated catechol was proposed. The total energies, dipole moments, structural molecular and reactivity parameters of the conformers and transition states involved were calculated. These theoretical magnitudes were correlated with properties of the solvating solvents. The properties of solute-solvent association complexes formed by a molecule of catechol and three molecules of water by means of intermolecular hydrogen bonds were also calculated. Conclusions. The stability of the conformer that has one intramolecular hydrogen bond increases with the hydrogen-bond donor capability and polarity of the solvents. The dipole moment of catechol in water (11.45 D) is due to the solute-solvent association complexes, which are the predominant forms of the compound in aqueous solutions.Fil: Rudyk, Roxana Amelia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica. Cátedra de Química General.; ArgentinaFil: Molina, María A. A.. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica. Cátedra de Química General.; ArgentinaFil: Gómez, María Inés. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica. Cátedra de Química General.; 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; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química. Área de Química Física; ArgentinaFil: Ferretti, Ferdinando Hector. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química. Área de Química Física; ArgentinaBioChem Press2004-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/138819Rudyk, Roxana Amelia; Molina, María A. A.; Gómez, María Inés; Blanco, Sonia Encarnacion; Ferretti, Ferdinando Hector; Structure and dipole moment of catechol in hydroxylic solvents; BioChem Press; Internet Electronic Journal of Molecular Design; 3; 1; 1-2004; 11-281538-6414CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.biochempress.com/av03_0011.htmlinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:26:59Zoai:ri.conicet.gov.ar:11336/138819instacron: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:34982025-10-15 14:26:59.969CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Structure and dipole moment of catechol in hydroxylic solvents
title Structure and dipole moment of catechol in hydroxylic solvents
spellingShingle Structure and dipole moment of catechol in hydroxylic solvents
Rudyk, Roxana Amelia
Catechol
Conformations
Dipole moment
Hydrogen bonding
Solvent effects
Association complexes
DFT calculations
title_short Structure and dipole moment of catechol in hydroxylic solvents
title_full Structure and dipole moment of catechol in hydroxylic solvents
title_fullStr Structure and dipole moment of catechol in hydroxylic solvents
title_full_unstemmed Structure and dipole moment of catechol in hydroxylic solvents
title_sort Structure and dipole moment of catechol in hydroxylic solvents
dc.creator.none.fl_str_mv Rudyk, Roxana Amelia
Molina, María A. A.
Gómez, María Inés
Blanco, Sonia Encarnacion
Ferretti, Ferdinando Hector
author Rudyk, Roxana Amelia
author_facet Rudyk, Roxana Amelia
Molina, María A. A.
Gómez, María Inés
Blanco, Sonia Encarnacion
Ferretti, Ferdinando Hector
author_role author
author2 Molina, María A. A.
Gómez, María Inés
Blanco, Sonia Encarnacion
Ferretti, Ferdinando Hector
author2_role author
author
author
author
dc.subject.none.fl_str_mv Catechol
Conformations
Dipole moment
Hydrogen bonding
Solvent effects
Association complexes
DFT calculations
topic Catechol
Conformations
Dipole moment
Hydrogen bonding
Solvent effects
Association complexes
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 Motivation. Various classes of flavonoids of great importance for medicine have a molecular structure containing a resorcinol in its A-ring whereas the B-ring is a catechol derivative. With a future view to establishing correlations between the physicochemical and biological properties of flavonoids and catechols and with the specific aim of explaining the dipole moment of catechol in water, we investigated the molecular conformations and solute-solvent interactions of catechol in ethanol, methanol and water. Method. Basis sets at two levels of theory: HF/6-31G(d,p) and B3LYP/6-31G(d,p) were used for calculations. Onsager's method was used to analyze the solvent effects on the conformers of catechol. Results. A conformational equilibrium between the two main conformers of non-solvated catechol was proposed. The total energies, dipole moments, structural molecular and reactivity parameters of the conformers and transition states involved were calculated. These theoretical magnitudes were correlated with properties of the solvating solvents. The properties of solute-solvent association complexes formed by a molecule of catechol and three molecules of water by means of intermolecular hydrogen bonds were also calculated. Conclusions. The stability of the conformer that has one intramolecular hydrogen bond increases with the hydrogen-bond donor capability and polarity of the solvents. The dipole moment of catechol in water (11.45 D) is due to the solute-solvent association complexes, which are the predominant forms of the compound in aqueous solutions.
Fil: Rudyk, Roxana Amelia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica. Cátedra de Química General.; Argentina
Fil: Molina, María A. A.. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica. Cátedra de Química General.; Argentina
Fil: Gómez, María Inés. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorgánica. Cátedra de Química General.; 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. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química. Área de Química Física; Argentina
Fil: Ferretti, Ferdinando Hector. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química. Área de Química Física; Argentina
description Motivation. Various classes of flavonoids of great importance for medicine have a molecular structure containing a resorcinol in its A-ring whereas the B-ring is a catechol derivative. With a future view to establishing correlations between the physicochemical and biological properties of flavonoids and catechols and with the specific aim of explaining the dipole moment of catechol in water, we investigated the molecular conformations and solute-solvent interactions of catechol in ethanol, methanol and water. Method. Basis sets at two levels of theory: HF/6-31G(d,p) and B3LYP/6-31G(d,p) were used for calculations. Onsager's method was used to analyze the solvent effects on the conformers of catechol. Results. A conformational equilibrium between the two main conformers of non-solvated catechol was proposed. The total energies, dipole moments, structural molecular and reactivity parameters of the conformers and transition states involved were calculated. These theoretical magnitudes were correlated with properties of the solvating solvents. The properties of solute-solvent association complexes formed by a molecule of catechol and three molecules of water by means of intermolecular hydrogen bonds were also calculated. Conclusions. The stability of the conformer that has one intramolecular hydrogen bond increases with the hydrogen-bond donor capability and polarity of the solvents. The dipole moment of catechol in water (11.45 D) is due to the solute-solvent association complexes, which are the predominant forms of the compound in aqueous solutions.
publishDate 2004
dc.date.none.fl_str_mv 2004-01
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/11336/138819
Rudyk, Roxana Amelia; Molina, María A. A.; Gómez, María Inés; Blanco, Sonia Encarnacion; Ferretti, Ferdinando Hector; Structure and dipole moment of catechol in hydroxylic solvents; BioChem Press; Internet Electronic Journal of Molecular Design; 3; 1; 1-2004; 11-28
1538-6414
CONICET Digital
CONICET
url http://hdl.handle.net/11336/138819
identifier_str_mv Rudyk, Roxana Amelia; Molina, María A. A.; Gómez, María Inés; Blanco, Sonia Encarnacion; Ferretti, Ferdinando Hector; Structure and dipole moment of catechol in hydroxylic solvents; BioChem Press; Internet Electronic Journal of Molecular Design; 3; 1; 1-2004; 11-28
1538-6414
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.biochempress.com/av03_0011.html
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 BioChem Press
publisher.none.fl_str_mv BioChem Press
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 13.22299

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