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Effective Solvent Cavity for 1-Hydroxy-9,10-anthraquinone Derivatives in Methanol/Water, Using a Local QSAR Study Method

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Abstract

The Onsager reaction field model was applied to 1-hydroxy-9,10-anthraquinone derivatives dissolved in binary solvent mixtures of methanol/water. Each solution was placed in a cavity surrounded by a continuous dielectric constant medium, and then the quantum chemical descriptors of the solute were calculated. Multiple linear regression was used to perform the QSPR model calculations in order to predict the acidity constants of the solutes. The resultant hexa-parametric model was able to predict the acidity constants within absolute average deviations less than 1.82 %. The proposed model suggests that the acidic property of the solute is controlled by solvation processes through coulombic interactions as well as orbital energies. It was found that the solvent lowered the excited orbital energy states of all 1-hydroxy-9,10-anthraquinone derivatives. The model proposes that an effective solvation cavity needs more methanol molecules than water in order to increase the solvation energy in the solution.

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Abbreviations

N :

Number of components

R 2 :

Correlation coefficient

SE:

Standard error of regression

F :

Fisher’s F-ratio

\(Q_{\mathrm{LOO}}^{2}\) :

Correlation coefficients of leave-one-out cross-validations

\(Q_{\mathrm{LTO}}^{2}\) :

Correlation coefficients of leave-three-out cross-validations

pK a :

Acidity constant

AQ:

Anthraquinone derivatives

rms:

Root mean square

s:

Surface potential

a:

Acidity

LOO:

Leave one out

LTO:

Leave three out

+:

Positive potential energy surface value

−:

Negative potential energy surface value

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Acknowledgements

The authors thank the Research Council of Zabol University for supporting this project. M. Sanchooli is thankful to Dr. Bahram Hemmateenejad for his constructive discussion and recommendations.

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  1. Chemistry Department, University of Zabol, Zabol, Iran

    Mahmood Sanchooli & Zohreh Razmara

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  1. Mahmood Sanchooli
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  2. Zohreh Razmara
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Correspondence to Mahmood Sanchooli.

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Sanchooli, M., Razmara, Z. Effective Solvent Cavity for 1-Hydroxy-9,10-anthraquinone Derivatives in Methanol/Water, Using a Local QSAR Study Method. J Solution Chem 41, 1290–1298 (2012). https://doi.org/10.1007/s10953-012-9882-8

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  • DOI: https://doi.org/10.1007/s10953-012-9882-8

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