McCurdy, Alison and Jimenez, Leslie and Stauffer, David A. and Dougherty, Dennis A. (1992) Biomimetic catalysis of S_N2 reactions through cation-π interactions. The role of polarizability in catalysis. Journal of the American Chemical Society, 114 (26). pp. 10314-10321. ISSN 0002-7863. doi:10.1021/ja00052a031. https://resolver.caltech.edu/CaltechAUTHORS:20170809-104140484
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Abstract
Cyclophane hosts 1 and 2 have been shown to be effective catalysts for both the alkylation of quinoline structures to produce quinolinium salts and the dealkylation of sulfonium salts to produce sulfides. Thus, reactions that develop positive charge in the transition state and reactions that destroy positive charge are accelerated. The former observation is not surprising, given the well-documented ability of these hosts to bind cations through the cation-π interaction. The catalysis of the dealkylation reactions, however, along with several other observations, suggests that some other factor is involved in the catalysis. It is proposed that the high polarizability of the transition states is well matched to the very polarizable hosts and that this contributes to the catalysis.
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| Additional Information: | © 1992 American Chemical Society. This work was supported the by Office of Naval Research. A.M. was a Department of Education Graduate Assistance in Areas of National Need Fellow. We thank Richard E. Barrans, Jr., for many helpful discussions. | |||||||||
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| Issue or Number: | 26 | |||||||||
| DOI: | 10.1021/ja00052a031 | |||||||||
| Record Number: | CaltechAUTHORS:20170809-104140484 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20170809-104140484 | |||||||||
| Official Citation: | Biomimetic catalysis of SN2 reactions through cation-π interactions. The role of polarizability in catalysis Alison McCurdy, Leslie Jimenez, David A. Stauffer, and Dennis A. Dougherty Journal of the American Chemical Society 1992 114 (26), 10314-10321 DOI: 10.1021/ja00052a031 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 80013 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Tony Diaz | |||||||||
| Deposited On: | 09 Aug 2017 17:50 | |||||||||
| Last Modified: | 15 Nov 2021 17:52 |
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