The Journal of organic chemistry

Reactions of charged substrates. 5. The Solvolysis and sodium azide substitution reactions of benzylpyridinium ions in deuterium oxide

N Buckley, NJ Oppenheimer

Index: Buckley, Neil; Oppenheimer, Norman J. Journal of Organic Chemistry, 1996 , vol. 61, # 21 p. 7360 - 7372

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Citation Number: 20

Abstract

Second-order rate constants and activation values were measured for the reactions with NaN3 of a series of 4-Y-substituted (Y= MeO, Me, H, Cl, and NO2) benzyl 3'-Z-substituted (Z= CN, CONH2, H, F, Ac) pyridinium chlorides in deuterium oxide. 3'-Cyanopyridine substrates reacted much faster than nicotinamide and pyridine substrates; in the pyridine series the 4-Me, 4-H, and 4-Cl benzyl analogs did not react for up to 6 months at 96° C in ...