Is there an intramolecular hydrogen bond in 2-halophenols? A theoretical and spectroscopic investigation

Physical Chemistry Chemical Physics : PCCP
Michael H AbrahamClaudio F Tormena

Abstract

The Abraham solute hydrogen bond acidity parameter A can be derived both from physical methods, A(Gen) and NMR experiments, A(NMR) and results for a large number of hydroxylic solutes show that the two methods agreed very well. However for halophenols the values of A(NMR) were not consistent with the A(Gen) values. The values of A(NMR) suggest that there is no intra-molecular hydrogen bonding in any of the 2-halophenols. In contrast the values of A(Gen) indicate that there is no intra-molecular hydrogen bonding in 2-fluorophenol, but weak intra-molecular hydrogen bonding in 2-chloro, 2-bromo, and 2-iodo-phenol. In view of this uncertainty in the presence or absence of intra-molecular H-bonds in the 2-halophenols, a detailed investigation of the methods used in the literature is presented together with a novel NMR method to determine the ratio of cis and trans forms in these compounds. The experimental data is complemented by a detailed theoretical analysis of the structures and bonding in these molecules to assess the presence or absence of an intra-molecular H-bond. We conclude that there is weak hydrogen bonding in 2-chloro, 2-bromo and 2-iodophenol but very little in 2-fluorophenol.

References

Jun 25, 2004·Journal of Chromatography. a·Michael H AbrahamAndreas M Zissimos
Apr 22, 2006·The Journal of Organic Chemistry·Michael H AbrahamLee Griffiths
Aug 31, 2007·Magnetic Resonance in Chemistry : MRC·Raymond J Abraham, Mehdi Mobli
Sep 24, 2009·Journal of Pharmaceutical Sciences·Michael H AbrahamWilliam E Acree
Apr 17, 2010·Journal of the American Chemical Society·Erin R JohnsonWeitao Yang
Apr 26, 2011·Journal of Chemical Theory and Computation·Julia Contreras-GarcíaWeitao Yang
Jan 8, 2013·Organic & Biomolecular Chemistry·Vassiliki G KontogianniIoannis P Gerothanassis
May 16, 2014·Magnetic Resonance in Chemistry : MRC·Raymond J AbrahamManuel Perez
Sep 23, 2014·Chemosphere·Michael H Abraham, William E Acree

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Citations

Aug 31, 2016·Progress in Nuclear Magnetic Resonance Spectroscopy·Cláudio F Tormena
May 28, 2016·Physical Chemistry Chemical Physics : PCCP·Raymond J Abraham, M Ashley Cooper
Jul 13, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ben E SmithGregory S Tschumper
Jun 3, 2017·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Robin Taylor
Aug 10, 2019·The Journal of Physical Chemistry. a·Robert E Rosenberg
Jun 21, 2018·Biochemistry·Anna-Carin C CarlssonP Shing Ho
Apr 20, 2018·The Journal of Physical Chemistry. a·Robert E Rosenberg
Aug 15, 2019·Journal of Chemical Information and Modeling·Christoph A Bauer
Jul 19, 2019·Accounts of Chemical Research·Asia Marie S RielPui Shing Ho
Nov 13, 2020·The Journal of Physical Chemistry. a·Graham A CooperMichael N R Ashfold
Apr 6, 2019·The Journal of Physical Chemistry. a·A J Lopes JesusR Fausto

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