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Polar intermolecular interactions encoded in partitioncoefficients :an indirect estimation of hydrogenbond parameters of polyfunctional solutes 

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Published in  Journal of Physical Chemistry. 1992, vol. 96, no. 3, p. 14551459  
Abstract  Lipophilicity (expressed as log P, the logarithm of partition coefficients) is known to be decomposable into a cavity/volume term V expressing mainly hydrophobic and dispersive solutesolvent interactions, and polar terms reflecting electrostatic solutesolvent interactions, e.g. log P = aV + bpi* + calpha + dbeta, where pi*, alpha, and beta are solvatochromic parameters, i.e., the dipolarity/polarizability, Hbond donor acidity, and Hbond acceptor basicity, respectively. Here, we define a parameter LAMBDA such that LAMBDA = bpi* + calpha + dbeta and show that LAMBDA(oct) (i.e., LAMBDA calculated from 1octanol/water log P values) is correlated mainly with beta (r2 = 0.867; n = 168), while LAMBDA(alk) (i.e., LAMBDAcalculated from alkane/water log P values) is correlated mainly with alpha and beta (r2 = 0.897; n = 104). Thus, and within the explored range of values, a fair estimate of the Hbond donor acidity and acceptor basicity of solutes can be obtained from their log P(oct) and log P(alk) values and calculated molecular volumes  
Identifiers  DOI: 10.1021/j100182a078  
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Citation (ISO format)  EL TAYAR, Nabil, TESTA, Bernard, CARRUPT, PierreAlain. Polar intermolecular interactions encoded in partitioncoefficients :an indirect estimation of hydrogenbond parameters of polyfunctional solutes. In: Journal of Physical Chemistry, 1992, vol. 96, n° 3, p. 14551459. doi: 10.1021/j100182a078 https://archiveouverte.unige.ch/unige:10572 