Hydrogen Bonding between Solutes in Solvents Octan-1-ol and Water

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This article discusses hydrogen bonding between solutes in solvents octan-1-ol and water.

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8 p.

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Abraham, M. H. (Michael H.); Gola, Joelle R. M.; Cometto-Muñiz, J. Enrique & Acree, William E. (William Eugene) October 18, 2010.

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This article discusses hydrogen bonding between solutes in solvents octan-1-ol and water.

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8 p.

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

Abstract: The 1:1 equilibrium constants, K, for the association of hydrogen bond bases and hydrogen bond acids have been determined by using octan-1-ol solvent at 298 K for 30 acid−base combinations. The values of K are much smaller than those found for aprotic, rather nonpolar solvents. It is shown that the log K values can satisfactorily be correlated against αH2·βH2, where αH2 and βH2 are the 1:1 hydrogen bond acidities and basicities of solutes. The slope of the plot, 2.938, is much smaller than those for log K values in the nonpolar organic solvents previously studied. An analysis of literature data on 1:1 hydrogen bonding in water yields a negative slope for a plot of log K against αH2·βH2, thus showing how the use of very strong hydrogen bond acids and bases does not lead to larger values of log K for 1:1 hydrogen bonding in water. It is suggested that for simple 1:1 association between monofunctional solutes in water, log K cannot be larger than about −0.1 log units. Descriptors have been obtained for the complex between 2,2,2-trifluoroethanol and propanone, and used to analyze solvent effects on the two reactants, the complex, and the complexation constant.

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  • Journal of Organic Chemistry, 2010, Washington D.C.: American Chemical Society, pp. 7651-7658

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  • Publication Title: Journal of Organic Chemistry
  • Volume: 75
  • Issue: 22
  • Page Start: 7651
  • Page End: 7658
  • Peer Reviewed: Yes

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  • October 18, 2010

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  • July 24, 2013, 1:20 p.m.

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  • Jan. 9, 2015, 5:18 p.m.

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Abraham, M. H. (Michael H.); Gola, Joelle R. M.; Cometto-Muñiz, J. Enrique & Acree, William E. (William Eugene). Hydrogen Bonding between Solutes in Solvents Octan-1-ol and Water, article, October 18, 2010; [Washington, D.C.]. (digital.library.unt.edu/ark:/67531/metadc174724/: accessed December 17, 2018), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT College of Arts and Sciences.