Network of secondary-substituted adamantane amines

Abstract

The set of 42 diastereomeric structures resulting from various degrees of substitution of secondary -CH2- groups by amines -NH- within the adamantane skeleton are investigated. They are placed into a substitution-reaction network viewed as a partial ordering, and the resultant reaction network (or Hasse diagram) displayed to illustrate different features. Ground-state ab-initio total energies of the 42 species are computed. A systematic cluster expansion of these total energies and associated internal energies is described in the context of this partial ordering. The results given support the idea, that recognition of the partial ordering is worthwhile. Copyright © 2013 John Wiley & Sons, Ltd.