Solute Descriptors for Phenoxide Anions and Their Use to Establish Correlations of Rates of Reaction of Anions with Iodomethane

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Article on solute descriptors for phenoxide anions and their use to establish correlations of rates of reaction of anions with iodomethane.

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6 p.

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Abraham, M. H. (Michael H.) & Acree, William E. (William Eugene) April 9, 2010.

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Article on solute descriptors for phenoxide anions and their use to establish correlations of rates of reaction of anions with iodomethane.

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6 p.

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Reprinted with permission from the Journal of Organic Chemistry. Copyright 2010 American Chemical Society.

Abstract: Partition coefficients from water to organic solvents for phenoxide anions have been obtained using a method based on the variation of pKa of phenols with solvent. From these partition coefficients, the Abraham descriptors for phenoxide anions, on the same scale as descriptors for neutral molecules, have been obtained. Equations have been constructed for the prediction of descriptors, and values of the Abraham descriptors E, S, A (equal to zero for the phenoxide anions we have studied), B, V, and J− have been determined or estimated for some 60 substituted phenoxide anions. These anions are characterized by very large values of the dipolarity/polarizability descriptor S and the hydrogen bond basicity descriptor B. In order to show the utility of the obtained phenoxide descriptors, we demonstrate that they can be combined with descriptors for carboxylate anions and permanent anions to yield equations for the Finkelstein reaction of anions with iodomethane in methanol, N,N-dimethylformamide, and water.

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  • Journal of Organic Chemistry, 2010, Washington DC: American Chemical Society, pp. 3021-3026

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  • Publication Title: Journal of Organic Chemistry
  • Volume: 75
  • Issue: 9
  • Page Start: 3021
  • Page End: 3026
  • Peer Reviewed: Yes

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  • April 9, 2010

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  • July 24, 2013, 1:20 p.m.

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  • Feb. 24, 2014, 3:44 p.m.

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Abraham, M. H. (Michael H.) & Acree, William E. (William Eugene). Solute Descriptors for Phenoxide Anions and Their Use to Establish Correlations of Rates of Reaction of Anions with Iodomethane, article, April 9, 2010; [Washington, DC]. (digital.library.unt.edu/ark:/67531/metadc174720/: accessed April 22, 2018), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT College of Arts and Sciences.