Inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): Temperature, solvent effects and molecular modeling
A thermodynamic study of the inclusion process between 2-chlorobenzophenone (2ClBP) and cyclomaltoheptaose (β-cyclodextrin, β-CD) was performed using UV-vis spectroscopy, reversed-phase liquid chromatography (RP-HPLC), and molecular modeling (PM6). Spectrophotometric measurements in aqueous solution...
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2011
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n13_p1978_Sancho http://hdl.handle.net/20.500.12110/paper_00086215_v346_n13_p1978_Sancho |
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paper:paper_00086215_v346_n13_p1978_Sancho2023-06-08T14:32:59Z Inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): Temperature, solvent effects and molecular modeling 2-Chlorobenzophenone Apparent formation constants Molecular modeling Reversed-phase liquid chromatography Solubility β-Cyclodextrin Chromatography Cyclodextrins Enthalpy Molecular modeling Solubility Solutions Solvents Temperature Temperature distribution Ultraviolet visible spectroscopy 2-Chlorobenzophenone Formation constants Mobile-phase composition Reversed phase liquid-chromatography Semi-empirical methods Spectrophotometric measurements Temperature dependence Thermodynamic parameter Liquid chromatography 2 chlorobenzophenone benzophenone derivative beta cyclodextrin unclassified drug article controlled study drug solubility encapsulation enthalpy entropy molecular model priority journal reversed phase high performance liquid chromatography solvent effect stoichiometry temperature thermodynamics ultraviolet spectroscopy A thermodynamic study of the inclusion process between 2-chlorobenzophenone (2ClBP) and cyclomaltoheptaose (β-cyclodextrin, β-CD) was performed using UV-vis spectroscopy, reversed-phase liquid chromatography (RP-HPLC), and molecular modeling (PM6). Spectrophotometric measurements in aqueous solutions were performed at different temperatures. The stoichiometry of the complex is 1:1 and its apparent formation constant (Kc) is 3846 M-1 at 30 °C. Temperature dependence of Kc values revealed that both enthalpy (δH° = -10.58 kJ/mol) and entropy changes (δS° = 33.76 J/K mol) are favorable for the inclusion process in an aqueous medium. Encapsulation was also investigated using RP-HPLC (C18 column) with different mobile-phase compositions, to which β-CD was added. The apparent formation constants in MeOH-H2O (KF) were dependent of the proportion of the mobile phase employed (50:50, 55:45, 60:40 and 65:35, v/v). The KF values were 419 M-1 (50% MeOH) and 166 M -1 (65% MeOH) at 30 °C. The thermodynamic parameters of the complex in an aqueous MeOH medium indicated that this process is largely driven by enthalpy change (δH° = -27.25 kJ/mol and δS° = -45.12 J/K mol). The results of the study carried out with the PM6 semiempirical method showed that the energetically most favorable structure for the formation of the complex is the 'head up' orientation. © 2011 Elsevier Ltd. All rights reserved. 2011 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n13_p1978_Sancho http://hdl.handle.net/20.500.12110/paper_00086215_v346_n13_p1978_Sancho |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
2-Chlorobenzophenone Apparent formation constants Molecular modeling Reversed-phase liquid chromatography Solubility β-Cyclodextrin Chromatography Cyclodextrins Enthalpy Molecular modeling Solubility Solutions Solvents Temperature Temperature distribution Ultraviolet visible spectroscopy 2-Chlorobenzophenone Formation constants Mobile-phase composition Reversed phase liquid-chromatography Semi-empirical methods Spectrophotometric measurements Temperature dependence Thermodynamic parameter Liquid chromatography 2 chlorobenzophenone benzophenone derivative beta cyclodextrin unclassified drug article controlled study drug solubility encapsulation enthalpy entropy molecular model priority journal reversed phase high performance liquid chromatography solvent effect stoichiometry temperature thermodynamics ultraviolet spectroscopy |
| spellingShingle |
2-Chlorobenzophenone Apparent formation constants Molecular modeling Reversed-phase liquid chromatography Solubility β-Cyclodextrin Chromatography Cyclodextrins Enthalpy Molecular modeling Solubility Solutions Solvents Temperature Temperature distribution Ultraviolet visible spectroscopy 2-Chlorobenzophenone Formation constants Mobile-phase composition Reversed phase liquid-chromatography Semi-empirical methods Spectrophotometric measurements Temperature dependence Thermodynamic parameter Liquid chromatography 2 chlorobenzophenone benzophenone derivative beta cyclodextrin unclassified drug article controlled study drug solubility encapsulation enthalpy entropy molecular model priority journal reversed phase high performance liquid chromatography solvent effect stoichiometry temperature thermodynamics ultraviolet spectroscopy Inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): Temperature, solvent effects and molecular modeling |
| topic_facet |
2-Chlorobenzophenone Apparent formation constants Molecular modeling Reversed-phase liquid chromatography Solubility β-Cyclodextrin Chromatography Cyclodextrins Enthalpy Molecular modeling Solubility Solutions Solvents Temperature Temperature distribution Ultraviolet visible spectroscopy 2-Chlorobenzophenone Formation constants Mobile-phase composition Reversed phase liquid-chromatography Semi-empirical methods Spectrophotometric measurements Temperature dependence Thermodynamic parameter Liquid chromatography 2 chlorobenzophenone benzophenone derivative beta cyclodextrin unclassified drug article controlled study drug solubility encapsulation enthalpy entropy molecular model priority journal reversed phase high performance liquid chromatography solvent effect stoichiometry temperature thermodynamics ultraviolet spectroscopy |
| description |
A thermodynamic study of the inclusion process between 2-chlorobenzophenone (2ClBP) and cyclomaltoheptaose (β-cyclodextrin, β-CD) was performed using UV-vis spectroscopy, reversed-phase liquid chromatography (RP-HPLC), and molecular modeling (PM6). Spectrophotometric measurements in aqueous solutions were performed at different temperatures. The stoichiometry of the complex is 1:1 and its apparent formation constant (Kc) is 3846 M-1 at 30 °C. Temperature dependence of Kc values revealed that both enthalpy (δH° = -10.58 kJ/mol) and entropy changes (δS° = 33.76 J/K mol) are favorable for the inclusion process in an aqueous medium. Encapsulation was also investigated using RP-HPLC (C18 column) with different mobile-phase compositions, to which β-CD was added. The apparent formation constants in MeOH-H2O (KF) were dependent of the proportion of the mobile phase employed (50:50, 55:45, 60:40 and 65:35, v/v). The KF values were 419 M-1 (50% MeOH) and 166 M -1 (65% MeOH) at 30 °C. The thermodynamic parameters of the complex in an aqueous MeOH medium indicated that this process is largely driven by enthalpy change (δH° = -27.25 kJ/mol and δS° = -45.12 J/K mol). The results of the study carried out with the PM6 semiempirical method showed that the energetically most favorable structure for the formation of the complex is the 'head up' orientation. © 2011 Elsevier Ltd. All rights reserved. |
| title |
Inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): Temperature, solvent effects and molecular modeling |
| title_short |
Inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): Temperature, solvent effects and molecular modeling |
| title_full |
Inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): Temperature, solvent effects and molecular modeling |
| title_fullStr |
Inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): Temperature, solvent effects and molecular modeling |
| title_full_unstemmed |
Inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): Temperature, solvent effects and molecular modeling |
| title_sort |
inclusion complex of 2-chlorobenzophenone with cyclomaltoheptaose (β-cyclodextrin): temperature, solvent effects and molecular modeling |
| publishDate |
2011 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n13_p1978_Sancho http://hdl.handle.net/20.500.12110/paper_00086215_v346_n13_p1978_Sancho |
| _version_ |
1768541966882045952 |