The reaction mechanism for the organocatalytic ring-opening polymerization of L-lactide using a guanidine-based catalyst: Hydrogen-bonded or covalently bound?

被引：230

作者：

Chuma, Anthony ^{[1
]}

Horn, Hans W. ^{[1
]}

Swope, William C. ^{[1
]}

Pratt, Russell C. ^{[2
]}

Zhang, Lei ^{[3
]}

Lohmeijer, Bas G. G. ^{[4
]}

Wade, Charles G. ^{[1
]}

Waymouth, Robert M. ^{[5
]}

Hedrick, James L. ^{[1
]}

Rice, Julia E. ^{[1
]}

机构：

[1] IBM Almaden Res Ctr, San Jose, CA 95032 USA

[2] Seeo Inc, Berkeley, CA 94710 USA

[3] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

[4] BASF SE, Global Polymer Res Div, D-67056 Ludwigshafen, Germany

[5] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 21期

关键词：

D O I：

10.1021/ja0764411

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have investigated two alternative mechanisms for the ring-opening polymerization of L-lacticle using a guanidine-based catalyst, the first involving acetyl transfer to the catalyst, and the second involving only hydrogen bonding to the catalyst. Using computational chemistry methods, we show that the hydrogen bonding pathway is considerably preferred over the acetyl transfer pathway and that this is consistent with experimental information.

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页码：6749 / 6754

页数：6

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