Aromaticity and tautomerism—VII: Empirical resonance energy and conjugation energy of pyrazole and isoxazole from heats of dehydration data |
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| Authors: | Andrew V Chapman Michael J Cook Alan R Katritzky Michael H Aabraham Angela F Danil De Namor Lilane Dumont Jacques Reisse |
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| Institution: | School of Chemical Sciences, University of East Anglia, Norwich NR4 7TJ, England;Department of Chemistry, University of Surrey, Guildford GU2 5XH, Surrey, England;Faculté des Sciences Appliquées, Service de Chimie Organique E.P., Avenue F.-D. Roosevelt, 50,1050 Bruxelles, Belgium |
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| Abstract: | The dehydration of various 4,5-dihydro-4- and -5-hydroxy derivatives of pyrazole and isoxazole has been investigated. Heats of dehydration of 4,5-duiydro-4-hydroxy-1,3,5-tripbenylpyrazole and 4,5-dihydro-5-hydroxy-isoxazole are evaluated and used to assess the empirical resonance energy and conjugation energy of pyrazole and isoxazole. The former possesses resonance stabilisation comparable to pyrrole but that of the latter is low. |
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