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The Reaction Mechanism for the Organocatalytic Ring-Opening Polymerization of l-Lactide Using a Guanidine-Based Catalyst: Hydrogen-Bonded or Covalently Bound?
Abstract
We have investigated two alternative mechanisms for the ring-opening polymerization of l-lactide 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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Citations
Cites
Controlled Ring-Opening Polymerization of Lactide and Glycolide
Dechy-Cabaret, O., Martin-Vaca, B., & Bourissou, D. (2004) · Chemical Reviews · doi:10.1021/cr040002s · Cited by 2,257
Cited by
Synthesis of polycaprolactone: A review
Labet, M., & Thielemans, W. (2009) · Chemical Society Reviews · doi:10.1039/b820162p · Cited by 1,673
Organocatalysis: Opportunities and Challenges for Polymer Synthesis
Kiesewetter, M. K., Shin, E. J., Hedrick, J. L., & Waymouth, R. M. (2010) · Macromolecules · doi:10.1021/ma9025948 · Cited by 907
Self-citationUrea Anions: Simple, Fast, and Selective Catalysts for Ring-Opening Polymerizations
Lin, B., & Waymouth, R. M. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.6b11864 · Cited by 278
Self-citationZwitterionic Ring-Opening Polymerization for the Synthesis of High Molecular Weight Cyclic Polymers
Brown, H. A., & Waymouth, R. M. (2013) · Accounts of Chemical Research · doi:10.1021/ar400072z · Cited by 255
Self-citationBouyahyi, M., Pepels, M. P. F., Heise, A., & Duchateau, R. (2012) · Macromolecules · doi:10.1021/ma3001675 · Cited by 157
Metadata
- Authors
- Chuma, A., Horn, H. W., Swope, W. C., Pratt, R. C., Zhang, L., Lohmeijer, B. G. G., Wade, C. G., Waymouth, R. M., Hedrick, J. L., & Rice, J. E.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-05-01
- Volume
- 130
- Issue
- 21
- Pages
- 6749-6754
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2036129919
- Cited by
- 282
- References
- 1
- FWCI
- 7.18
- Type
- journal article
- Language
- en
- Open access
- closed
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- The paper
- Chuma, A., Horn, H. W., Swope, W. C., Pratt, R. C., Zhang, L., Lohmeijer, B. G. G., Wade, C. G., Waymouth, R. M., Hedrick, J. L., & Rice, J. E. (2008). The Reaction Mechanism for the Organocatalytic Ring-Opening Polymerization of l-Lactide Using a Guanidine-Based Catalyst: Hydrogen-Bonded or Covalently Bound? Journal of the American Chemical Society. https://doi.org/10.1021/ja0764411
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
