The DOI matches its Crossref record; 2 of the 2 references it cites were found in a registry or an index.
Using Kamlet−Taft Solvent Descriptors To Explain the Reactivity of Anionic Nucleophiles in Ionic Liquids
Abstract
In this paper, we report the effect of ionic liquids on substitution reactions using a variety of anionic nucleophiles. We have combined new studies of the reactivity of polyatomic anions, acetate, trifuoroacetate, cyanide, and thiocyanide, with our previous studies of the halides in [C4C1py][Tf2N], [C4C1py][TfO], and [C4C1im][Tf2N] (where [C4C1im]+ is 1-butyl-3-methylimidazolium and [C4C1py]+ is 1-butyl-1-methylpyrrolidinium) and compared their reactivities, k2, to the same reactions in the molecular solvents dichloromethane, dimethylsulfoxide, and methanol. The Kamlet-Taft solvent descriptors (alpha, beta, pi) have been used to analyze the rates of the reactions, which were found to have a strong inverse dependency on the alpha value of the solvent. This result is attributed to the ability of the solvent to hydrogen bond to the nucleophile, so reducing its reactivity. The Eyring activation parameters (DeltaH++ and DeltaS++), while confirming the reaction mechanism, do not offer obvious correlations with the Kamlet-Taft solvent descriptors.
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Cammarata, L., Kazarian, S. G., Salter, P. A., & Welton, T. (2001) · Physical Chemistry Chemical Physics · doi:10.1039/b106900d · Cited by 1,441
Self-citationIonic liquids: solvent properties and organic reactivity
Chiappe, C., & Pieraccini, D. (2005) · Journal of Physical Organic Chemistry · doi:10.1002/poc.863 · Cited by 1,169
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Ionic liquids and catalysis: Recent progress from knowledge to applications
Olivier-Bourbigou, H., Magna, L., & Morvan, D. (2010) · Applied Catalysis A: General · doi:10.1016/j.apcata.2009.10.008 · Cited by 1,639
Room temperature ionic liquids as emerging solvents for the pretreatment of lignocellulosic biomass
Mora‐Pale, M., Meli, L., Doherty, T. V., Linhardt, R. J., & Dordick, J. S. (2011) · Biotechnology and Bioengineering · doi:10.1002/bit.23108 · Cited by 384
The effect of the ionic liquid anion in the pretreatment of pine wood chips
Brandt, A., Hallett, J. P., Leak, D. J., Murphy, R. J., & Welton, T. (2010) · Green Chemistry · doi:10.1039/b918787a · Cited by 333
Self-citationEsterification in Ionic Liquids: The Influence of Solvent Basicity
Wells, T. P., Hallett, J. P., Williams, C. K., & Welton, T. (2008) · The Journal of Organic Chemistry · doi:10.1021/jo8005864 · Cited by 65
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Metadata
- Authors
- Crowhurst, L., Falcone, R., Lancaster, N. L., Llopis-Mestre, V., & Welton, T.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-10-19
- Volume
- 71
- Issue
- 23
- Pages
- 8847-8853
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2022736016
- Cited by
- 164
- References
- 2
- FWCI
- 4.54
- Type
- journal article
- Language
- en
- Open access
- closed
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