Coenzyme models. 28. Facile oxidation of alcohols and amines by 3-hydroxy-N-methylacridinium ion, a new NAD+ model compound

S Shinkai, H Hamada, H Kuroda…

Index: Shinkai, Seiji; Hamada, Hisatake; Kuroda, Hideo; Manabe, Osamu Journal of Organic Chemistry, 1981 , vol. 46, # 11 p. 2333 - 2338

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Citation Number: 7

Abstract

It appears that substitutions of the type modeled here do not much affect the planar" Y" framework of the guanidinium ion. They do, however, noticeably perturb the magnitude of single rotational barriers. The barrier changes, compared with the guanidinium case, are small for substitution by a methyl group, f 2 kcal mol-', but are larger for fluoro and amino substitution, f10 kcal mol-l. The range of barrier changes is not unreasonable judged ...