Physicochemical and toxicological studies on 4-chloro-3,5-dinitrobenzoic acid in aqueous solutions

Autores
Lopez, Jorge. L; Garcia Einschlag, Fernando Sebastian; Rives, Carina V.; Villata, Laura S.; Capparelli, Alberto Luis
Año de publicación
2004
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Physicochemical characterization of hazardous compounds often is required for the development of structure-reactivity correlations. Physical, chemical, and toxicological properties of target pollutants require determination for an efficient application of wastewater treatments. In the present work, we chose a chloro-nitro-aromatic derivative (4-chloro-3,5-dinitrobenzoic acid [CDNBA]), as a model compound on which to perform physicochemical and toxicological studies. Several properties of CDNBA are not available in the literature, although many aromatic nitro-compounds are considered hazardous materials. Measurements of solubility in water, acid dissociation constant, and kinetic parameters for the nucleophilic substitution of chlorine atom in alkaline media are reported. We also performed cytotoxicity studies of CDNBA and ultraviolet-irradiated CDNBA solutions. From the analysis of CDNBA solubility in water at different temperatures, an enthalpy of solution of 23.2 ± 2.5 kJ/mol was found. The study of the acid dissociation constant Kc by using conductivity measurements and the modified Gran's method yielded values for the equilibrium constant Ka of 2.36 × 10-3 and 2.26 × 10 -3, respectively. The bimolecular rate constant for the reaction of CDNB- and hydroxyl ion (HO-) measured at room temperature and 0.1 M of ionic strength was 5.92/M·s, and the activation energy for this process was 70.7 ± 3.4 kJ/mol. Cytotoxicity assays with aqueous suspensions of Tetrahymena pyriformis showed lethal effects due to the pH change induced by CDNBA. On the other hand, in buffered solutions, a value of 104.47 μM was observed for the median effective concentration, that is, the concentration of CDNBA at which the proliferation was restricted to one half of the blank. Irradiation of CDNBA solutions increased the toxicity, suggesting the formation of intermediate products with higher cytotoxicity effects.
Fil: Lopez, Jorge. L. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Garcia Einschlag, Fernando Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Rives, Carina V.. Provincia de Buenos Aires. Administración General de Obras Sanitarias; Argentina
Fil: Villata, Laura S.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Capparelli, Alberto Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Materia
Cytotoxicity
Nitro Compounds
Physicochemical
Properties
Risk Assessment
Nivel de accesibilidad
acceso abierto
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https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
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CONICET Digital (CONICET)
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Consejo Nacional de Investigaciones Científicas y Técnicas
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oai:ri.conicet.gov.ar:11336/54439
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Physicochemical and toxicological studies on 4-chloro-3,5-dinitrobenzoic acid in aqueous solutionsLopez, Jorge. LGarcia Einschlag, Fernando SebastianRives, Carina V.Villata, Laura S.Capparelli, Alberto LuisCytotoxicityNitro CompoundsPhysicochemicalPropertiesRisk Assessmenthttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Physicochemical characterization of hazardous compounds often is required for the development of structure-reactivity correlations. Physical, chemical, and toxicological properties of target pollutants require determination for an efficient application of wastewater treatments. In the present work, we chose a chloro-nitro-aromatic derivative (4-chloro-3,5-dinitrobenzoic acid [CDNBA]), as a model compound on which to perform physicochemical and toxicological studies. Several properties of CDNBA are not available in the literature, although many aromatic nitro-compounds are considered hazardous materials. Measurements of solubility in water, acid dissociation constant, and kinetic parameters for the nucleophilic substitution of chlorine atom in alkaline media are reported. We also performed cytotoxicity studies of CDNBA and ultraviolet-irradiated CDNBA solutions. From the analysis of CDNBA solubility in water at different temperatures, an enthalpy of solution of 23.2 ± 2.5 kJ/mol was found. The study of the acid dissociation constant Kc by using conductivity measurements and the modified Gran's method yielded values for the equilibrium constant Ka of 2.36 × 10-3 and 2.26 × 10 -3, respectively. The bimolecular rate constant for the reaction of CDNB- and hydroxyl ion (HO-) measured at room temperature and 0.1 M of ionic strength was 5.92/M·s, and the activation energy for this process was 70.7 ± 3.4 kJ/mol. Cytotoxicity assays with aqueous suspensions of Tetrahymena pyriformis showed lethal effects due to the pH change induced by CDNBA. On the other hand, in buffered solutions, a value of 104.47 μM was observed for the median effective concentration, that is, the concentration of CDNBA at which the proliferation was restricted to one half of the blank. Irradiation of CDNBA solutions increased the toxicity, suggesting the formation of intermediate products with higher cytotoxicity effects.Fil: Lopez, Jorge. L. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Garcia Einschlag, Fernando Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Rives, Carina V.. Provincia de Buenos Aires. Administración General de Obras Sanitarias; ArgentinaFil: Villata, Laura S.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Capparelli, Alberto Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaSociety of Environmental Toxicology and Chemistry2004-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/54439Lopez, Jorge. L; Garcia Einschlag, Fernando Sebastian; Rives, Carina V.; Villata, Laura S.; Capparelli, Alberto Luis; Physicochemical and toxicological studies on 4-chloro-3,5-dinitrobenzoic acid in aqueous solutions; Society of Environmental Toxicology and Chemistry; Environmental Toxicology and Chemistry; 23; 5; 5-2004; 1129-11350730-7268CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1897/03-73info:eu-repo/semantics/altIdentifier/url/https://setac.onlinelibrary.wiley.com/doi/abs/10.1897/03-73info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:32:27Zoai:ri.conicet.gov.ar:11336/54439instacron: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 11:32:28.041CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Physicochemical and toxicological studies on 4-chloro-3,5-dinitrobenzoic acid in aqueous solutions
title Physicochemical and toxicological studies on 4-chloro-3,5-dinitrobenzoic acid in aqueous solutions
spellingShingle Physicochemical and toxicological studies on 4-chloro-3,5-dinitrobenzoic acid in aqueous solutions
Lopez, Jorge. L
Cytotoxicity
Nitro Compounds
Physicochemical
Properties
Risk Assessment
title_short Physicochemical and toxicological studies on 4-chloro-3,5-dinitrobenzoic acid in aqueous solutions
title_full Physicochemical and toxicological studies on 4-chloro-3,5-dinitrobenzoic acid in aqueous solutions
title_fullStr Physicochemical and toxicological studies on 4-chloro-3,5-dinitrobenzoic acid in aqueous solutions
title_full_unstemmed Physicochemical and toxicological studies on 4-chloro-3,5-dinitrobenzoic acid in aqueous solutions
title_sort Physicochemical and toxicological studies on 4-chloro-3,5-dinitrobenzoic acid in aqueous solutions
dc.creator.none.fl_str_mv Lopez, Jorge. L
Garcia Einschlag, Fernando Sebastian
Rives, Carina V.
Villata, Laura S.
Capparelli, Alberto Luis
author Lopez, Jorge. L
author_facet Lopez, Jorge. L
Garcia Einschlag, Fernando Sebastian
Rives, Carina V.
Villata, Laura S.
Capparelli, Alberto Luis
author_role author
author2 Garcia Einschlag, Fernando Sebastian
Rives, Carina V.
Villata, Laura S.
Capparelli, Alberto Luis
author2_role author
author
author
author
dc.subject.none.fl_str_mv Cytotoxicity
Nitro Compounds
Physicochemical
Properties
Risk Assessment
topic Cytotoxicity
Nitro Compounds
Physicochemical
Properties
Risk Assessment
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Physicochemical characterization of hazardous compounds often is required for the development of structure-reactivity correlations. Physical, chemical, and toxicological properties of target pollutants require determination for an efficient application of wastewater treatments. In the present work, we chose a chloro-nitro-aromatic derivative (4-chloro-3,5-dinitrobenzoic acid [CDNBA]), as a model compound on which to perform physicochemical and toxicological studies. Several properties of CDNBA are not available in the literature, although many aromatic nitro-compounds are considered hazardous materials. Measurements of solubility in water, acid dissociation constant, and kinetic parameters for the nucleophilic substitution of chlorine atom in alkaline media are reported. We also performed cytotoxicity studies of CDNBA and ultraviolet-irradiated CDNBA solutions. From the analysis of CDNBA solubility in water at different temperatures, an enthalpy of solution of 23.2 ± 2.5 kJ/mol was found. The study of the acid dissociation constant Kc by using conductivity measurements and the modified Gran's method yielded values for the equilibrium constant Ka of 2.36 × 10-3 and 2.26 × 10 -3, respectively. The bimolecular rate constant for the reaction of CDNB- and hydroxyl ion (HO-) measured at room temperature and 0.1 M of ionic strength was 5.92/M·s, and the activation energy for this process was 70.7 ± 3.4 kJ/mol. Cytotoxicity assays with aqueous suspensions of Tetrahymena pyriformis showed lethal effects due to the pH change induced by CDNBA. On the other hand, in buffered solutions, a value of 104.47 μM was observed for the median effective concentration, that is, the concentration of CDNBA at which the proliferation was restricted to one half of the blank. Irradiation of CDNBA solutions increased the toxicity, suggesting the formation of intermediate products with higher cytotoxicity effects.
Fil: Lopez, Jorge. L. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Garcia Einschlag, Fernando Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Rives, Carina V.. Provincia de Buenos Aires. Administración General de Obras Sanitarias; Argentina
Fil: Villata, Laura S.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Capparelli, Alberto Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
description Physicochemical characterization of hazardous compounds often is required for the development of structure-reactivity correlations. Physical, chemical, and toxicological properties of target pollutants require determination for an efficient application of wastewater treatments. In the present work, we chose a chloro-nitro-aromatic derivative (4-chloro-3,5-dinitrobenzoic acid [CDNBA]), as a model compound on which to perform physicochemical and toxicological studies. Several properties of CDNBA are not available in the literature, although many aromatic nitro-compounds are considered hazardous materials. Measurements of solubility in water, acid dissociation constant, and kinetic parameters for the nucleophilic substitution of chlorine atom in alkaline media are reported. We also performed cytotoxicity studies of CDNBA and ultraviolet-irradiated CDNBA solutions. From the analysis of CDNBA solubility in water at different temperatures, an enthalpy of solution of 23.2 ± 2.5 kJ/mol was found. The study of the acid dissociation constant Kc by using conductivity measurements and the modified Gran's method yielded values for the equilibrium constant Ka of 2.36 × 10-3 and 2.26 × 10 -3, respectively. The bimolecular rate constant for the reaction of CDNB- and hydroxyl ion (HO-) measured at room temperature and 0.1 M of ionic strength was 5.92/M·s, and the activation energy for this process was 70.7 ± 3.4 kJ/mol. Cytotoxicity assays with aqueous suspensions of Tetrahymena pyriformis showed lethal effects due to the pH change induced by CDNBA. On the other hand, in buffered solutions, a value of 104.47 μM was observed for the median effective concentration, that is, the concentration of CDNBA at which the proliferation was restricted to one half of the blank. Irradiation of CDNBA solutions increased the toxicity, suggesting the formation of intermediate products with higher cytotoxicity effects.
publishDate 2004
dc.date.none.fl_str_mv 2004-05
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/11336/54439
Lopez, Jorge. L; Garcia Einschlag, Fernando Sebastian; Rives, Carina V.; Villata, Laura S.; Capparelli, Alberto Luis; Physicochemical and toxicological studies on 4-chloro-3,5-dinitrobenzoic acid in aqueous solutions; Society of Environmental Toxicology and Chemistry; Environmental Toxicology and Chemistry; 23; 5; 5-2004; 1129-1135
0730-7268
CONICET Digital
CONICET
url http://hdl.handle.net/11336/54439
identifier_str_mv Lopez, Jorge. L; Garcia Einschlag, Fernando Sebastian; Rives, Carina V.; Villata, Laura S.; Capparelli, Alberto Luis; Physicochemical and toxicological studies on 4-chloro-3,5-dinitrobenzoic acid in aqueous solutions; Society of Environmental Toxicology and Chemistry; Environmental Toxicology and Chemistry; 23; 5; 5-2004; 1129-1135
0730-7268
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1897/03-73
info:eu-repo/semantics/altIdentifier/url/https://setac.onlinelibrary.wiley.com/doi/abs/10.1897/03-73
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
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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 Society of Environmental Toxicology and Chemistry
publisher.none.fl_str_mv Society of Environmental Toxicology and Chemistry
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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