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Descriptors for adamantane and some of its derivatives
Abraham, M.H. Acree, W.E. Jr Liu, Xiangli
Abraham, M.H.
Acree, W.E. Jr
Liu, Xiangli
Publication Date
2021-03-01
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© 2021 Elsevier. Reproduced in accordance with the publisher's self-archiving policy. This manuscript version is made available under the CC-BY-NC-ND 4.0 license (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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openAccess
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2020-11-25
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Abstract
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.
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Accepted manuscript
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Abraham MH, Acree, WE Jr and Liu X (2021) Descriptors for adamantane and some of its derivatives. Journal of Molecular Liquids. 325: 114894.
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