Steric and electronic effects of methyl substitutents at the 2-and 6-positions on N-benzyl-1, 4-dihydronicotinamide.

JUN TAKEDA, S OHTA, M HIROBE

Index: Takeda, Jun; Ohta, Shigeru; Hirobe, Masaaki Chemical & Pharmaceutical Bulletin, 1987 , vol. 35, # 7 p. 2661 - 2667

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Citation Number: 5

Abstract

N-Benzyl-1, 4-dihydronicotinamides having 2-methyl, 6-methyl and 2, 6-dimethyl substituents were prepared and their reactivities toward an activated carbonyl compound (hexachloroacetone) were investigated. The reaction rates were especially enhanced for the 2, 6-dimethyl derivative, with the order of the rates being 2, 6-dimethyl> 2-methyl> 6-methyl. The steric and electronic effects of the methyl group (s) are discussed based on the ...