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dc.contributor.authorAbraham, M.H.
dc.contributor.authorAbraham, R.J.
dc.contributor.authorAghamohammadi, Amin
dc.contributor.authorAfarinkia, Kamyar
dc.contributor.authorLiu, Xiangli
dc.date.accessioned2020-07-20T14:17:12Z
dc.date.accessioned2020-08-14T15:02:47Z
dc.date.available2020-07-20T14:17:12Z
dc.date.available2020-08-14T15:02:47Z
dc.date.issued2020-10
dc.identifier.citationAbraham 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.en_US
dc.identifier.urihttp://hdl.handle.net/10454/17969
dc.descriptionYesen_US
dc.description.abstractWe 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.en_US
dc.language.isoenen_US
dc.relation.isreferencedbyhttps://doi.org/10.1016/j.molliq.2020.113730en_US
dc.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.en_US
dc.subjectIntramolecular hydrogen bondingen_US
dc.subjectHydrogen bond acidityen_US
dc.subjectWater-solvent partition coefficientsen_US
dc.subjectLinear free energy relationshipen_US
dc.subject1H NMR chemical shiftsen_US
dc.titleThe assessment of intramolecular hydrogen bonding in ortho-substituted anilines by an NMR methoden_US
dc.status.refereedYesen_US
dc.date.Accepted2020-06-30
dc.date.application2020-07-03
dc.typeArticleen_US
dc.date.EndofEmbargo2021-07-04
dc.type.versionAccepted manuscripten_US
dc.description.publicnotesThe full-text of this article will be released for public view at the end of the publisher embargo on 04 Jul 2021.en_US
dc.date.updated2020-07-20T13:17:18Z
refterms.dateFOA2020-08-14T15:03:16Z


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