Steric effects on mesomerism VIII : Benzoquinuclidine, an aromatic amine without mesomeric interaction between the benzene ring and the amino group
- 1 January 1952
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 71 (12) , 1159-1170
- https://doi.org/10.1002/recl.19520711202
Abstract
The spatial configuration of benzoquinuclidine (I) is such as to justify on theoretical grounds the assumption that the mesomeric interaction between the amino group and the benzene ring is at a minimum. The experimental work reported here proves that this interaction is in fact essentially zero, and hence that, in general, elimination of mesomerism by steric factors is possible. This result was obtained by a study of ultraviolet absorption spectra and of the ability to couple with diazonium compounds.Keywords
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