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Manipulating Solute Nucleophilicity with Room Temperature Ionic Liquids
Abstract
In this work we report the effect of ionic liquids on a class of charge-neutral nucleophiles. We have studied the reactions of (n)butylamine, di-(n)butylamine, and tri-(n)butylamine with methyl p-nitrobenzenesulfonate in [bmpy][N(Tf)(2)], [bmpy][OTf], and [bmim][OTf] (bmpy = 1-butyl-1-methylpyrrolidinium; bmim = 1-butyl-3-methylimidazolium) and compared their reactivities, k(2), to those for the same reactions in the molecular solvents dichloromethane and acetonitrile. It was shown that all of the amines are more nucleophilic in the ionic liquids than in the molecular solvents studied in this work. Comparison is also made with the effect of ionic liquids on the reactivity of chloride ions, which are deactivated in ionic liquids. The Eyring activation parameters revealed that changes in the activation entropies are largely responsible for the effects seen. This can be explained in part by the differing hydrogen-bonding properties, as shown by the Kamlet-Taft solvent parameters, of each of these solvents and the formation of hydrogen bonds between the solvents and the nucleophiles.
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Cites
Cammarata, L., Kazarian, S. G., Salter, P. A., & Welton, T. (2001) · Physical Chemistry Chemical Physics · doi:10.1039/b106900d · Cited by 1,441
Self-citation
Cited by
Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2
Hallett, J. P., & Welton, T. (2011) · Chemical Reviews · doi:10.1021/cr1003248 · Cited by 12,578
Self-citationZhang, S., Zhang, J., Zhang, Y., & Deng, Y. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00509 · Cited by 659
Ohno, H., & Fukumoto, K. (2007) · Accounts of Chemical Research · doi:10.1021/ar700053z · Cited by 631
Methods for stabilizing and activating enzymes in ionic liquids—a review
Zhao, H. (2010) · Journal of Chemical Technology & Biotechnology · doi:10.1002/jctb.2375 · Cited by 351
Purification of imidazolium ionic liquids for spectroscopic applications
Nockemann, P., Binnemans, K., & Driesen, K. (2005) · Chemical Physics Letters · doi:10.1016/j.cplett.2005.08.128 · Cited by 261
Metadata
- Authors
- Crowhurst, L., Lancaster, N. L., Pérez Arlandis, J. M., & Welton, T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-08-27
- Volume
- 126
- Issue
- 37
- Pages
- 11549-11555
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1994765455
- Cited by
- 229
- References
- 1
- FWCI
- 8.91
- Type
- journal article
- Language
- en
- Open access
- closed
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