The Journal of Organic Chemistry

Heterocyclic aromatic anions with 4n+ 2. pi.-electrons

FG Bordwell, HE Fried

Index: Bordwell, Frederick G.; Fried, Herbert E. Journal of Organic Chemistry, 1991 , vol. 56, # 13 p. 4218 - 4223

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Citation Number: 182

Abstract

Equilibrium acidities in DMSO for several cyclic carboxamides, thiocarboxamides, esters, and sulfones that form anions possessing 4n+ 2 electrons have been measured. Aromatic stabilization energies (AS&) for these anions have been estimated by comparing their pKm values with those of open-chain analogues. The AS& (kcal/mol) are 8.3 for N-methylindolin- 2-one, 15.5 for N-methylindoline-2-thione, 7.1 for 2-oxo-2, 3-dihydrobenzo [b] furan, 8.5 for ...