TY - JOUR

T1 - Octanol-water partition coefficients of substituted phenols and their correlation with molecular descriptors

AU - Makovskaya, Valeria Vladimirovna

AU - Dean, John

AU - Tomlinson, William

AU - Comber, Michael

PY - 1995/10/30

Y1 - 1995/10/30

N2 - Quantum mechanical molecular descriptors and physical properties have been used to estimate log k(ow) values for a range of substituted phenols using multilinear regression. The quantum mechanical molecular descriptors were derived from a commercially available software package. Two models have been proposed. The first model involves molecular mass and E(HOMO) as independent variables whereas the second model combines the following molecular descriptors: molecular mass, melting point, charge on oxygen atom, E(HOMO), E(LUMO), molecular volume, total surface area, refractivity, and polarizability. The equations were derived using a set of 14 reference phenolic compounds with their log k(ow) values being the average of several experimental values reported in the literature. The predictive power of the derived model equations was compared to a set of 18 test compounds, whose log k(ow) values have been estimated by an isocratic liquid chromatography (LC) procedure. log k(ow) values of the test compounds estimated on the basis of the two equations showed good correlation with LC estimated log k(ow) values.

AB - Quantum mechanical molecular descriptors and physical properties have been used to estimate log k(ow) values for a range of substituted phenols using multilinear regression. The quantum mechanical molecular descriptors were derived from a commercially available software package. Two models have been proposed. The first model involves molecular mass and E(HOMO) as independent variables whereas the second model combines the following molecular descriptors: molecular mass, melting point, charge on oxygen atom, E(HOMO), E(LUMO), molecular volume, total surface area, refractivity, and polarizability. The equations were derived using a set of 14 reference phenolic compounds with their log k(ow) values being the average of several experimental values reported in the literature. The predictive power of the derived model equations was compared to a set of 18 test compounds, whose log k(ow) values have been estimated by an isocratic liquid chromatography (LC) procedure. log k(ow) values of the test compounds estimated on the basis of the two equations showed good correlation with LC estimated log k(ow) values.

KW - Molecular modelling

KW - multilinear regression

KW - octanol-water partition coefficient

KW - quantitative structure property relationships

KW - quantum mechanical molecular descriptors

U2 - 10.1016/0003-2670(95)00296-C

DO - 10.1016/0003-2670(95)00296-C

M3 - Article

SN - 0003-2670

VL - 315

SP - 193

EP - 200

JO - Analytica Chimica Acta

JF - Analytica Chimica Acta

IS - 1-2

ER -