Steric effects on mesomerism: XI, The ultra‐violet absorption spectrum of Tröger's base and the stereochemistry of aromatic amines
- 1 January 1953
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 72 (8) , 661-672
- https://doi.org/10.1002/recl.19530720806
Abstract
A careful analysis of molecular models shows that in Tröger's base (I) the configuration of the two aniline systems can be described as skewpyramidal with an angle of twist of 45°. The ultra‐violet spectrum of this compound reveals that in this configuration the mesomeric interaction between the benzene ring and the amino group is by no means eliminated. The consequences of this are discussed with respect to the connection between spatial configuration and mesomerism in aromatic amines, and are placed on a semi‐quantitative basis by comparison of oscillator strengths.The results obtained are utilized in a fairly detailed discussion of the stereochemistry of aromatic amines. Configurations with pyramidal nitrogen appear to be definitely more favourable from an energy point of view than configurations with planar nitrogen.Keywords
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