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    The assessment of intramolecular hydrogen bonding in ortho-substituted anilines by an NMR method

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    Publication date
    2020-10
    Author
    Abraham, M.H.
    Abraham, R.J.
    Aghamohammadi, Amin
    Afarinkia, Kamyar
    Liu, Xiangli
    Keyword
    Intramolecular hydrogen bonding
    Hydrogen bond acidity
    Water-solvent partition coefficients
    Linear free energy relationship
    1H NMR chemical shifts
    Rights
    © 2020 Elsevier B.V. All rights reserved. Reproduced in accordance with the publisher's self-archiving policy. This manuscript version is made available under the CC-BY-NC-ND 4.0 license.
    Peer-Reviewed
    Yes
    
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    Abstract
    We describe the Δlog P method for the assessment of intramolecular hydrogen bonds (IMHBs), and show that it is not a very general method of distinguishing between molecules in which there is an IMHB and molecules in which there is no IMHB. The ‘double’ Δlog P method of Shalaeva et al. is a much more reliable method for the assessment of IMHB but requires the synthesis of a model compound and the determination of no less than four water-solvent partition coefficients. In addition, it is difficult to apply to compounds that contain more than one hydrogen bond acidic group capable of IMHB. We then describe our NMR method of assessing IMHB, based on 1H NMR chemical shifts in solvents DMSO and CDCl3. We have determined 1H NMR chemical shifts for a number of ortho-substituted anilines and show that the only compound we have studied that forms an IMHB is methyl 2-methylaminobenzoate though there is no IMHB present in methyl 2-aminobenzoate. This apparently anomalous result is supported by both MM and ab initio calculations. The NMR method is much simpler and less time consuming than other methods for the assessment of IMHB. It provides a quantitative assessment of IMHB and can be applied to molecules with more than one hydrogen bond acidic group.
    URI
    http://hdl.handle.net/10454/17969
    Version
    Accepted manuscript
    Citation
    Abraham MH, Abraham RJ, Aghamohammadi A et al (2020) The assessment of intramolecular hydrogen bonding in ortho-substituted anilines by an NMR method. Journal of Molecular Liquids. 315: 113730.
    Link to publisher’s version
    https://doi.org/10.1016/j.molliq.2020.113730
    Type
    Article
    Collections
    Life Sciences Publications

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