Relationship between the calculated physicochemical parameters and reversed phase thin-layer chromatographic retention behavior of carboxamide fungicides and related compounds

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Abstract

The lipophilicity of 6 carboxamide fungicides and 11 phenylbenzamide derivatives were determined by reversed phase layer chromatography (RP-TLC) employing silica and alumina as stationary phases impregnated with paraffin oil. Mixtures of methanol-water, acetonitrile-water, tetrahydrofurane-water, and acetone-water were used as mobile phases. The RM0 and b values related to the molecular lipophilicity and to the specific hydrophobic surface area (b) of the solutes were calculated separately for each RP-TLC system and for each analyte. The correlations between the physicochemical parameters measured were calculated by linear regression analysis. The impact of the site and character of the substituent on the retention of analytes was assessed by Free-Wilson analysis. The measured lipophilicity parameters were compared with 24 molecular descriptors computed applying free engines of the web. Calculations proved that the character of the stationary phase and the type of organic modifier exerted a negligible effect on the measured lipophilicity parameters. In the majority of cases the RM0 and b values and computed molecular descriptors were intercorrelated, but the fitness of the points to the linear regression equation was not strong enough to replace the measured values with the computed ones. This finding indicates the importance of using not only computed but also measured parameters for the future studies of both quantitative structure retention relationship (QSRR) and quantitative structure activity relationship (QSAR) calculations.

Original languageEnglish
Pages (from-to)880-893
Number of pages14
JournalJournal of Liquid Chromatography and Related Technologies
Volume33
Issue number7-8
DOIs
Publication statusPublished - Jan 2010

Fingerprint

Fungicides
Water
Linear regression
Linear Models
Quantitative Structure-Activity Relationship
Aluminum Oxide
Reverse-Phase Chromatography
Acetone
Chromatography
Regression analysis
Silicon Dioxide
Methanol
Regression Analysis
Engines
Derivatives

Keywords

  • Carboxamide fungicides
  • Lipophilicity
  • Phenylbenzamide derivatives
  • Reversed phase thin-layer chromatography
  • Specific hydrophobic surface area

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmaceutical Science
  • Biochemistry
  • Clinical Biochemistry

Cite this

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title = "Relationship between the calculated physicochemical parameters and reversed phase thin-layer chromatographic retention behavior of carboxamide fungicides and related compounds",
abstract = "The lipophilicity of 6 carboxamide fungicides and 11 phenylbenzamide derivatives were determined by reversed phase layer chromatography (RP-TLC) employing silica and alumina as stationary phases impregnated with paraffin oil. Mixtures of methanol-water, acetonitrile-water, tetrahydrofurane-water, and acetone-water were used as mobile phases. The RM0 and b values related to the molecular lipophilicity and to the specific hydrophobic surface area (b) of the solutes were calculated separately for each RP-TLC system and for each analyte. The correlations between the physicochemical parameters measured were calculated by linear regression analysis. The impact of the site and character of the substituent on the retention of analytes was assessed by Free-Wilson analysis. The measured lipophilicity parameters were compared with 24 molecular descriptors computed applying free engines of the web. Calculations proved that the character of the stationary phase and the type of organic modifier exerted a negligible effect on the measured lipophilicity parameters. In the majority of cases the RM0 and b values and computed molecular descriptors were intercorrelated, but the fitness of the points to the linear regression equation was not strong enough to replace the measured values with the computed ones. This finding indicates the importance of using not only computed but also measured parameters for the future studies of both quantitative structure retention relationship (QSRR) and quantitative structure activity relationship (QSAR) calculations.",
keywords = "Carboxamide fungicides, Lipophilicity, Phenylbenzamide derivatives, Reversed phase thin-layer chromatography, Specific hydrophobic surface area",
author = "G. Oros and T. Cserh{\'a}ti",
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pages = "880--893",
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AU - Cserháti, T.

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N2 - The lipophilicity of 6 carboxamide fungicides and 11 phenylbenzamide derivatives were determined by reversed phase layer chromatography (RP-TLC) employing silica and alumina as stationary phases impregnated with paraffin oil. Mixtures of methanol-water, acetonitrile-water, tetrahydrofurane-water, and acetone-water were used as mobile phases. The RM0 and b values related to the molecular lipophilicity and to the specific hydrophobic surface area (b) of the solutes were calculated separately for each RP-TLC system and for each analyte. The correlations between the physicochemical parameters measured were calculated by linear regression analysis. The impact of the site and character of the substituent on the retention of analytes was assessed by Free-Wilson analysis. The measured lipophilicity parameters were compared with 24 molecular descriptors computed applying free engines of the web. Calculations proved that the character of the stationary phase and the type of organic modifier exerted a negligible effect on the measured lipophilicity parameters. In the majority of cases the RM0 and b values and computed molecular descriptors were intercorrelated, but the fitness of the points to the linear regression equation was not strong enough to replace the measured values with the computed ones. This finding indicates the importance of using not only computed but also measured parameters for the future studies of both quantitative structure retention relationship (QSRR) and quantitative structure activity relationship (QSAR) calculations.

AB - The lipophilicity of 6 carboxamide fungicides and 11 phenylbenzamide derivatives were determined by reversed phase layer chromatography (RP-TLC) employing silica and alumina as stationary phases impregnated with paraffin oil. Mixtures of methanol-water, acetonitrile-water, tetrahydrofurane-water, and acetone-water were used as mobile phases. The RM0 and b values related to the molecular lipophilicity and to the specific hydrophobic surface area (b) of the solutes were calculated separately for each RP-TLC system and for each analyte. The correlations between the physicochemical parameters measured were calculated by linear regression analysis. The impact of the site and character of the substituent on the retention of analytes was assessed by Free-Wilson analysis. The measured lipophilicity parameters were compared with 24 molecular descriptors computed applying free engines of the web. Calculations proved that the character of the stationary phase and the type of organic modifier exerted a negligible effect on the measured lipophilicity parameters. In the majority of cases the RM0 and b values and computed molecular descriptors were intercorrelated, but the fitness of the points to the linear regression equation was not strong enough to replace the measured values with the computed ones. This finding indicates the importance of using not only computed but also measured parameters for the future studies of both quantitative structure retention relationship (QSRR) and quantitative structure activity relationship (QSAR) calculations.

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