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
- 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:11336/54439
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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 Técnicas2025-09-29T10:02:55Zoai: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:34982025-09-29 10:02:55.774CONICET 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 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 |
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) |
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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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13.070432 |