13C-1H coupling constants as a conformational tool for structural assignment of quinic and octulosonic Acid
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A complete set of NMR coupling constants (1JC-H, 2JC-H, 3JC-H, and 3JH-H) were calculated for the eight stereoisomers of quinic acid, at the B3LYP/6-311G(d,p)/PCM(methanol) level of theory. The Fermi contact term of the coupling constants was computed with a modified, uncontracted, version of the 6-311G(d,p) basis set, with additional tight polarization functions. 1H and 13C NMR chemical shifts were determined at the same level using the gauge-invariant atomic orbital (GIAO) method. The magnitude of the spin-spin coupling constants was found to be affected by the orientation (axial or equatorial) of the coupling proton and the orientation of the hydroxy group on the coupling carbon, whereas the chemical shifts depend on the presence or absence of electron-withdrawing hydroxy groups attached to the carbon atoms involved.
Hameed , R , van Mourik , T & Khan , A 2018 , ' 13 C- 1 H coupling constants as a conformational tool for structural assignment of quinic and octulosonic Acid ' , Journal of Molecular Modeling , vol. 24 , no. 11 , 324 . https://doi.org/10.1007/s00894-018-3866-6
Journal of Molecular Modeling
© The Author(s) 2018. This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
DescriptionRH acknowledges funding from the Higher Education Commission of Pakistan for her visit to University of St-Andrews, as a visiting scholar. AK is thankful to the Higher Education Commission of Pakistan (Grant No. 1691) as well as to the COMSATS University Islamabad, Abbottabad Campus for financial support.
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