Carbinolamides are formed by the reaction of an amide and an aldehyde/ketone with an accompanying proton shift.  Interest in their chemistry has been fueled by their intermediacy in the enzyme catalyzed synthesis of a-amidated peptides and in many other biological venues.  Mechanistic studies of the aqueous reaction of these compounds have produced an interesting spectrum of reactivity.  More recently an increasing number of O-alkylated carbinolamides have been isolated that have interesting biological function.  The methods by which these compounds accomplish their biological function is unknown and this is, in part, due to a complete lack of knowledge as to the mechanisms by which these compounds react in solution. The purpose of the work presented here was to synthesize a number of O-alkylated carbinolamide derivatives of benzamide and acetamide,  and study their breakdown in water as a function of pH.   The acid-catalyzed rate constants for the carbinolamide derivatives will be discussed, along with two kinetically viable mechanisms of breakdown.

Structure/Reactivity studies of O-alkyl carbinolamides in water as function of pH

243rd National Meeting (2012)

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