Protonated Benzofuran, Anthracene, Naphthalene, Benzene, Ethene, and Ethyne: Measurements and Estimates of p K a and p KR

…, CM McDonnell, RA More O'Ferrall…

Index: McCormack, Aoife C.; McDonnell, Claire M.; More O'Ferrall, Rory A.; O'Donoghue, AnnMarie C.; Rao, S. Nagaraja Journal of the American Chemical Society, 2002 , vol. 124, # 29 p. 8575 - 8583

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Citation Number: 10

Abstract

Aqueous solvolyses of acyl derivatives of hydrates (water adducts) of anthracene and benzofuran yield carbocations which undergo competitive deprotonation to form the aromatic molecules and nucleophilic reaction with water to give the aromatic hydrates. Trapping experiments with azide ions yield rate constants kp for the deprotonation and k H2O for the nucleophilic reaction based on the “azide clock”. Combining these with rate ...