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A theoretical study on the alkali metal carboxylate‐promoted L‐Lactide polymerization
Author(s) -
Ozen Cihan,
Satoh Toshifumi,
Maeda Satoshi
Publication year - 2020
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.26386
Subject(s) - carboxylate , chemistry , moiety , lactide , substituent , polymerization , reaction mechanism , ring opening polymerization , polymer chemistry , bond cleavage , alkali metal , catalysis , organic chemistry , polymer
Sodium acetate‐catalyzed L‐lactide polymerization reaction is a simple yet efficient reaction. It provides a robust system to produce poly(L‐lactide) in industrial scale. In this study, the mechanism of this reaction has been studied by means of computational chemistry tools based on the experimental results. Basically, the mechanism consists of two steps: lactide coordination and ring opening through O‐Acyl bond cleavage. Additionally, the effect of cation size and substituent on carboxylate moiety have been evaluated. The calculations indicate that the larger cation leads to faster reactions. Moreover, the stronger electron‐donating group on carboxylate moiety accelerates the reaction rates. To obtain further insights, an orbital analysis has been also carried out. Our calculations are consistent with experimental findings and clarify underlying mechanistic features of the present reaction.