Abraham Michael H, Acree William E, Cometto-Muñiz J Enrique
Department of Chemistry, University College London, 20 Gordon Street, London WC1H OAJ, UK.
New J Chem. 2009;33(10):2034-2043. doi: 10.1039/b907118k.
Literature data on partitioning of compounds from the gas phase to a number of amides and from water to the amides has been collected and analyzed through the Abraham solvation equations. The resulting equations are statistically good enough to be used for the prediction of further partition coefficients, and allow deductions to be made about the chemical properties of the amides, as solvents. For example, tertiary amides have no hydrogen bond property at all, secondary amides are rather weak hydrogen bond acids, and primary amides are stronger hydrogen bond acids than are alcohols as solvents. Equations for partitioning from the gas phase to amide solvents can also be used to test if the amides are possible models for a number of biological phases and biological processes. It is shown that no organic solvent is a suitable model for phases such as blood, brain, muscle, liver, heart or kidney, but that a number of rather non-polar solvents are models for fat. N-methylformamide is shown to be the best (and excellent) model for eye irritation and nasal pungency in humans, suggesting that the receptor site in these processes is protein-like.
已通过亚伯拉罕溶剂化方程收集并分析了关于化合物从气相分配到多种酰胺以及从水分配到酰胺的文献数据。所得方程在统计学上足够好，可用于预测进一步的分配系数，并能对作为溶剂的酰胺的化学性质进行推断。例如，叔酰胺根本没有氢键性质，仲酰胺是相当弱的氢键酸，而伯酰胺作为溶剂时是比醇更强的氢键酸。从气相分配到酰胺溶剂的方程也可用于测试酰胺是否可能是一些生物相和生物过程的模型。结果表明，没有有机溶剂是血液、大脑、肌肉、肝脏、心脏或肾脏等相的合适模型，但一些相当非极性的溶剂是脂肪的模型。N - 甲基甲酰胺被证明是人类眼睛刺激和鼻腔刺激性的最佳（且出色）模型，这表明这些过程中的受体位点类似蛋白质。
