Rate and mode of basic hydrolysis of anhydropenicillin

✍ Scribed by Hans Bundgaard; Helle R. Angelo

• Book ID: 104242926
• Publisher: Elsevier Science
• Year: 1974
• Tongue: French
• Weight: 203 KB
• Volume: 15
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)91804-0

✦ Synopsis

The great sensitivity of the B-lactam moiety of biologically active penicillins and cephalosporins to attack by nucleophiles has been attributed mainly to a suppression of the usual amide resonance resulting from the nonplanarity in the f3-lactam nitrogen atomlf2.

Ease of basic hydrolysis of the B-lactam amide bond can be correlated with the degree of nonplanarity as well as with the f3-lactam stretching frequency3'4. A notable exception is apparently constituted by anhydropenicillins.