13C-1H coupling constants as a conformational tool for structural assignment of quinic and octulosonic Acid

Rabia Hameed, Tanja van Mourik, Afsar Khan

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4 Citations (Scopus)
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Abstract

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.
Original languageEnglish
Article number324
JournalJournal of Molecular Modeling
Volume24
Issue number11
Early online date26 Oct 2018
DOIs
Publication statusPublished - Nov 2018

Keywords

  • 13C-1H coupling constant
  • Quinic acid
  • Stereoisomers
  • Octulosonic acid
  • Relative stabilities
  • Density functional theory

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