Mathematical correlation of naproxen solubilities in organic solvents with the Abraham solvation parameter model

被引:31
作者
Daniels, CR
Charlton, AK
Wold, RM
Pustejovsky, E
Furman, AN
Bilbrey, AC
Love, JN
Garza, JA
Acree, WE
Abraham, MH
机构
[1] Univ N Texas, Dept Chem, Denton, TX 76203 USA
[2] UCL, Dept Chem, London WC1H 0AJ, England
基金
美国国家科学基金会;
关键词
naproxen solubilities; alcohol solvents; partition coefficients; molecular solute descriptors;
D O I
10.1080/00319100410001224520
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The Abraham solvation parameter model is used to calculate the numerical values of the solute descriptors for naproxen from experimental solubilities in organic solvents. The solute descriptors are denoted as follows: E is the solute excess molar refraction, V is McGowan volume of the solute, A and B are measures of the solute hydrogen-bond acidity and hydrogen-bond basicity, respectively, S is the solute dipolarity/polarizability descriptor and L is the logarithm of solute gas phase dimensionless Ostwald partition coefficient into hexadecane at 298 K. We estimate E as 1.510 and calculate V as 1.7821, and then solve a total of 40 equations to yield S = 2.022, A = 0.600, B = 0.673 and L = 9.207. These descriptors reproduce the observed log solubility ratios to within a standard deviation of only 0.073 log units.
引用
收藏
页码:481 / 491
页数:11
相关论文
共 47 条
[1]   Hydrogen bonding. 47. Characterization of the ethylene glycol-heptane partition system: Hydrogen bond acidity and basicity of peptides [J].
Abraham, MH ;
Martins, F ;
Mitchell, RC ;
Salter, CJ .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1999, 88 (02) :241-247
[2]   Correlation and estimation of gas-chloroform and water-chloroform partition coefficients by a linear free energy relationship method [J].
Abraham, MH ;
Platts, JA ;
Hersey, A ;
Leo, AJ ;
Taft, RW .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1999, 88 (07) :670-679
[3]   Solvation descriptors for ferrocene, and the estimation of some physicochemical and biochemical properties [J].
Abraham, MH ;
Benjelloun-Dakhama, N ;
Gola, JMR ;
Acree, WE ;
Cain, WS ;
Cometto-Muniz, JE .
NEW JOURNAL OF CHEMISTRY, 2000, 24 (10) :825-829
[5]   The determination of solvation descriptors for terpenes, and the prediction of nasal pungency thresholds [J].
Abraham, MH ;
Kumarsingh, R ;
Cometto-Muniz, JE ;
Cain, WS ;
Roses, M ;
Bosch, E ;
Diaz, ML .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (11) :2405-2411
[6]   Correlation and prediction of the solubility of Buckminster-fullerene in organic solvents; estimation of some physicochemical properties [J].
Abraham, MH ;
Green, CE ;
Acree, WE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (02) :281-286
[7]   The correlation and prediction of the solubility of compounds in water using an amended solvation energy relationship [J].
Abraham, MH ;
Le, J .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1999, 88 (09) :868-880
[8]   THE USE OF CHARACTERISTIC VOLUMES TO MEASURE CAVITY TERMS IN REVERSED PHASE LIQUID-CHROMATOGRAPHY [J].
ABRAHAM, MH ;
MCGOWAN, JC .
CHROMATOGRAPHIA, 1987, 23 (04) :243-246
[9]   Hydrogen bonding. Part 45. The solubility of gases and vapours in methanol at 298 K: An LFER analysis [J].
Abraham, MH ;
Whiting, GS ;
Carr, PW ;
Ouyang, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (06) :1385-1390
[10]   The solubility of gases and vapours in ethanol - the connection between gaseous solubility and water-solvent partition [J].
Abraham, MH ;
Whiting, GS ;
Shuely, WJ ;
Doherty, RM .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1998, 76 (06) :703-709