Citation: Guo-Hua CHEN, Ning JIANG, Hai-Yan XIANG, Hai-Bo DU. Theoretical Analysis of Structural Characteristics of Morin Rearrangement for Cephalosporins Prepared from Penicillin Sulfoxide[J]. Chinese Journal of Structural Chemistry, ;2020, 39(9): 1594-1600. doi: 10.14102/j.cnki.0254-5861.2011-2641 shu

Theoretical Analysis of Structural Characteristics of Morin Rearrangement for Cephalosporins Prepared from Penicillin Sulfoxide

College of Chemical Engineering, Sichuan University of Science & Engineering, Zigong 643000, China

Corresponding author: Guo-Hua CHEN, chgh29@163.com
Received Date: 15 October 2019
Accepted Date: 23 December 2019

Fund Project: Key Laboratories of Fine Chemicals and Surfactants in Sichuan Provincial Universities 2016JXY01the Opening Project of Key Laboratory of Green Chemistry of Sichuan Institutes of Higher Education LYJ1105Sichuan University of Science and Engineering talent introduction fund 2017RCL19

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The structure of penicillin sulfoxide is rearranged to cephalosporins by the Morin rearrangement. It is a unit reaction for the preparation of various types of cephalosporins. In order to make better use of the reaction and in view of the shortage of the reaction theory, this study used m062x/6-311++G (d, p) to explore the possible ring-opening reaction of the penicillin sulfoxide. It is found that the isomer of (S)-sulfoxide is a necessary structure. At the same time, the intramolecular hydrogen bonding effect between the side-chain amide proton (-CONH-) and the sulfinyl oxygen (-SO) is the decisive structure factor for the formation of alkenyl in ring-opening reaction, and the best reaction path is S0- > TS2- > IN1 channel. The main effect of acid catalysis is to catalyze the dehydration reaction of sulfenic acid to form sulfur cations for subsequently ring closing reaction.
- penicillin G sulfoxide,
- morin rearrangement,
- reaction mechanism,
- theoretical study,
- cephalosporins
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