LINEAR FREE-ENERGY RELATIONSHIP BETWEEN PARTITION COEFFICIENTS AND AQUEOUS SOLUBILITY OF ORGANIC LIQUIDS
LINEAR FREE-ENERGY RELATIONSHIP BETWEEN PARTITION COEFFICIENTS AND AQUEOUS SOLUBILITY OF ORGANIC LIQUIDS
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DOI：
10.1021/jo01265a071
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发表时间：
1968-01-01
影响因子：
3.6
通讯作者：
LAWRENCE, GL
中科院分区：
文献类型：
--
作者：
HANSCH, C;QUINLAN, JE;LAWRENCE, GL
本文表明，有机液体的水溶性的对数与其辛醇-水分配系数之间存在线性关系。由于配分系数的对数是有机分子的加性本构性质，因此可以计算未测量配分系数的液体的水溶性。或者，我们可以简单地为有机液体的水溶性建立一个类似于降落伞值或摩尔折射率的常数表。在物理生物化学和药理学中，一个日益重要的问题是选择合适的溶剂对（水和极性液体）来作为生物系统中水相和脂相的模型。我们一直在使用整个分子或部分分子的辛醇-水分配系数来估计这种体系中疏水键的相对强度。目前的研究表明，除了碳氢化合物外，几乎任何单功能液体，如醇、烷基卤化物、酯、酮等，都可以得到类似的结果，代表脂质相。自从meyer3和Overton 4的经典工作以来，关注化学结构与生物活性相关性的科学家一直在寻找合适的溶剂来近似活组织的水相和脂肪相。我们已经用1-辛醇和水得到了可以作为疏水键常数的分配系数。当与合适的电子和空间常数相结合时，这些将形成生化系统中结构-活性关系的多参数方法的基础。6
In this report it is shown that there is a linear relationshipbetween the logarithms of the aqueous solubilities of organic liquids and their octanol-waterpartition coefficients. Since the logarithm of the partition coefficient is an additive-constitutive property of organic molecules, the water solubility of liquids whose partition coefficients have not been measured can be calculated. Or, one can simply construct a table of constants for the water solubility of organic liquids analogous to parachor values or molar refractivities. A problem of increasing importance in physical biochemistry and pharmacology is the selection of a suitable solvent pair (water and an apolar liquid) to serve as a model for the aqueous and lipid phases in biological systems. We have been using octanol-water partition coefficients for whole molecules or parts of molecules to estimate relative strengths of hydrophobic bonding in such systems. The present study would indicate that, with the exception of hydrocarbons, one could expect similar results from almost any monofunctional liquid, such as an alcohol, alkyl halide, ester, ketone, etc., representing the lipid phase.Since the classic work of Meyer3and Overton, 4 scientists concerned with the correlation of chemical structure with biological activity have been seeking suitable solvents to approximate the aqueous and fatty phases of living tissue. We have been using 1-octanol and water to obtain partition coefficients which could serve as hydrophobic bonding constants. When combined with suitable electronicand steric constants, these would form the basis for a multiple-parameter approach to structure-activity relationships in biochemical systems. 6