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Classical conformational analysis of strained organic molecules. I. [ l , m , n ]Propellanes with l , m , n equal to 2, 3, and 4
Author(s) -
Dodziuk Helena
Publication year - 1984
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.540050610
Subject(s) - propellane , chemistry , octane , bicyclic molecule , computational chemistry , additive function , molecule , stereochemistry , crystallography , mathematics , organic chemistry , mathematical analysis
Abstract Classical conformational analysis was applied to the study of the variation of heats of formation ( HOF ) and geometrical parameters of small‐ring propellanes. As expected, the calculated HOF is the smallest for [4,4,4] propellane I and the largest for [2,2,2]propellane X. In spite of the different trends exhibited by the strain energy components, the calculated HOF values may be reproduced within a simple additivity scheme. The calculated bridgehead–bridgehead bond length is the longest for [2,2,2]propellane (1.655 Å), lowers with increasing molecular size, and is equal to 1.558 Å for [4,4,4]propellane. In agreement with experimental findings the latter value is significantly larger than the standard value of 1.54 Å typical for unstrained hydrocarbons. Other calculated geometrical parameters as well as HOF values cannot be compared with experimental and/or theoretical results since there is a lack of reliable experimental data. Surprisingly, [2,2,2]propellane was found to be more flexible than the less strained bicyclo[2,2,2]octane.