An NMR Method for Quantitative Assessment of Intramolecular Hydrogen Bonding; Application to Physiochemical, Environmental, and Biochemical Properties

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Article on an NMR method for the quantitative assessment of intramolecular hydrogen bonding and an application to physiochemical, environmental, and biochemical properties.

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9 p.

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Abraham, M. H. (Michael H.); Abraham, Raymond J.; Acree, William E. (William Eugene); Aliev, Abil E.; Leo, Albert J. & Whaley, William L. October 30, 2014.

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Article on an NMR method for the quantitative assessment of intramolecular hydrogen bonding and an application to physiochemical, environmental, and biochemical properties.

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9 p.

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Abstract: 1H NMR chemical shifts have been obtained in the solvents deuterochloroform and dimethyl sulfoxide. The difference in the chemical shifts of an OH or NH group in these two solvents, Δδ = δ(DMSO) – δ(CDCl3), can be converted into the hydrogen bond acidity, A, of the group using the equation A = 0.0065 + 0.133Δδ. The NMR A value, ANMR, can be used as a quantitative assessment of intramolecular hydrogen bonding. We list values of Δδ and ANMR for 55 compounds containing an OH group and 60 compounds with an NH group. For the hydroxy compounds, if A > 0.5 then the OH group is not part of an intramolecular hydrogen bond, but if A < 0.1 then the OH group forms part of an intramolecular hydrogen bond. For NH compounds, if A > 0.16 the NH group is not part of an intramolecular hydrogen bond, and if A < 0.05 the NH group is part of an intramolecular hydrogen bond. No comparison compounds are needed, and the method is extremely simple. We further show how it is possible to relate intramolecular hydrogen bonding to the actual effect on values of a number of physicochemical, environmental, and biochemical properties.

Reprinted with permission from the Journal of Organic Chemistry. Copyright 2014 American Chemical Society.

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  • Journal of Organic Chemistry, 2014, Washington D.C.: American Chemical Society, pp. 11075-11083

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  • Publication Title: Journal of Organic Chemistry
  • Volume: 79
  • Issue: 22
  • Page Start: 11075
  • Page End: 11083
  • Peer Reviewed: Yes

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Materials from the UNT community's research, creative, and scholarly activities and UNT's Open Access Repository. Access to some items in this collection may be restricted.

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  • October 30, 2014

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  • Dec. 4, 2014, 2:16 p.m.

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  • July 3, 2015, 12:44 p.m.

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Abraham, M. H. (Michael H.); Abraham, Raymond J.; Acree, William E. (William Eugene); Aliev, Abil E.; Leo, Albert J. & Whaley, William L. An NMR Method for Quantitative Assessment of Intramolecular Hydrogen Bonding; Application to Physiochemical, Environmental, and Biochemical Properties, article, October 30, 2014; [Washington, D.C.]. (digital.library.unt.edu/ark:/67531/metadc461727/: accessed November 23, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT College of Arts and Sciences.