Abstract
By analysis of data available in the literature of the degradation of penicillin G in acidic aqueous solution, it is shown that two reactions are involved. One is the acid catalyzed hydrolysis of the undissociated penicillin molecule to form penilloic acid. The second is rearrangement of the penicillin ion following attack by proton or the kinetically equivalent uncatalyzed reaction of undissociated penicillin to form penicillenic acid which rearranges to penillic acid. The significance of this mechanism is discussed.
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