Descriptors for adamantane and some of its derivatives

Literature data on solubilities of adamantane in organic solvents have been used to obtain properties, or descriptors. of adamantane. There is much less data on substituted adamantanes but we have been able to obtain descriptors for some 40 substituted adamantanes. These descriptors can then be used to estimate a wide range of physicochemical, environmental and other properties of the adamantanes. For the first time, the water-solvent partition coefficient and the gas-solvent partition coefficient into a large range of solvents, can be estimated, the latter being equivalent to Henry's Law constants. A variety of other important properties can also be estimated. These include vapor pressures, enthalpies of vaporization and sublimation, partitions from air and from blood into biological tissues, and skin permeability from water. The descriptors themselves are not exceptional. Adamantane itself has a rather low dipolarity, zero hydrogen bond acidity and a very low hydrogen bond basicity, in common with other multicyclic aliphatic compounds. These lead to adamantane being a very hydrophobic compound, as is evident from our estimated water-octanol partition coefficient (C) 2020 Elsevier B.V. All rights reserved.

Automated summary

Literature data on solubilities of adamantane in organic solvents were utilized to derive descriptors for adamantane and substituted adamantanes, enabling the estimation of various physicochemical properties. This allowed for the first-time estimation of water-solvent and gas-solvent partition coefficients across a wide range of solvents, along with other properties such as vapor pressures, enthalpies, and skin permeability. The descriptors indicated adamantane's hydrophobic nature, with low dipolarity and hydrogen bond acidity.