Network of secondary-substituted adamantane amines

• Published in: Journal of physical organic chemistry Vol. 26; no. 11; pp. 917 - 926
• Main Authors: Panda, Anirban, Vijayakumar, Subramaniam, Klein, Douglas J., Ryzhov, Anton
• Format: Journal Article
• Language: English
• Published: Bognor Regis Blackwell Publishing Ltd 01.11.2013; Wiley Subscription Services, Inc
• Subjects: cluster expansion; diastereomeric secondary-substituted adamantane amines; Hasse diagram; least-squares analysis; partial ordering; poset average; symmetry group
• ISSN: 0894-3230; 1099-1395
• DOI: 10.1002/poc.3190

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. A set of 42 diastereomeric structures resulting from the secondary‐substituted adamantane skeleton are placed into a substitution‐reaction partial ordering. A systematic group‐function‐like cluster expansion of these total energies and associated internal energies are reported to support the idea of partial ordering as worthwhile.