The polar nature of 2,1,3‐benzoxadiazole, ‐benzothiadiazole, ‐benzoselenadiazole and derivatives as determined by their electric dipole moments
- 1 October 1973
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 10 (5) , 773-778
- https://doi.org/10.1002/jhet.5570100516
Abstract
Permanent electric dipole moments have been determined in benzene solutions at 25° for the oxygen, sulfur, and selenium series of 2,1,3‐benzodiazoles. The derivatives studied contained 4, 5, and 6 substituted methyl, chloro, nitro, and amino groups. The dipole moment data of the derivatives were analyzed relative to that of the parent species which allowed deductions to be made about the mesomeric structures operating in the compounds. The mesomeric charge transfer increases regularly from the oxygen to the selenium structures, being nearly undetected in 2,1,3‐benzoxadiazole derivatives and very pronounced in the 2,1,3‐benzoselenadiazoles.Keywords
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