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Coordination Insertion Mechanism of Ring‐Opening Polymerization of Lactide Catalyzed by Stannous Octoate †
Author(s) -
Rao Weihan,
Cai Caiyun,
Tang Jingyu,
Wei Yiman,
Gao Caiyun,
Yu Lin,
Ding Jiandong
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000519
Subject(s) - chemistry , polymerization , lactide , polyester , catalysis , polymer , ring opening polymerization , ring (chemistry) , polymer chemistry , density functional theory , oxygen atom , combinatorial chemistry , organic chemistry , molecule , computational chemistry
Main observation and conclusion Ring‐opening polymerization (ROP) of cyclic esters in the presence of stannous octoate (Sn(Oct) 2 ) is the main way to obtain biodegradable aliphatic polyesters, an important family of biodegradable polymers which have been widely used and still rapidly developed in the fields of biomedical polymers and environment‐friendly materials. The underlying mechanism is thought via a coordination‐insertion way, but the pathway is still open owing to the absence of direct experimental evidence. Herein, we inquire this issue through density functional theory (DFT) calculations. According to our DFT calculations and the following Curtin‐Hammett evaluation, the carbonyl oxygen has a significant advantage over the ester oxygen, and thus the ring is opened mainly through pathway A instead of pathway B. The stannous octoate is identified as a catalyst rather than an initiator. We eventually summarize the main stages during the whole polymerization of lactide.