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

Rabia Hameed; Tanja van Mourik; Afsar Khan

doi:10.1007/s00894-018-3866-6

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

Rabia Hameed, Tanja van Mourik, Afsar Khan

Research output: Contribution to journal › Article › peer-review

Abstract

A complete set of NMR coupling constants (¹J_C-H, ²J_C-H, ³J_C-H, and ³J_H-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 language	English
Article number	324
Journal	Journal of Molecular Modeling
Volume	24
Issue number	11
Early online date	26 Oct 2018
DOIs	https://doi.org/10.1007/s00894-018-3866-6
Publication status	Published - Nov 2018

Keywords

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

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

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. ",

keywords = "13C-1H coupling constant, Quinic acid, Stereoisomers, Octulosonic acid, Relative stabilities, Density functional theory",

author = "Rabia Hameed and {van Mourik}, Tanja and Afsar Khan",

note = "RH 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.",

year = "2018",

month = nov,

doi = "10.1007/s00894-018-3866-6",

language = "English",

volume = "24",

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T1 - 13C-1H coupling constants as a conformational tool for structural assignment of quinic and octulosonic Acid

AU - Hameed, Rabia

AU - van Mourik, Tanja

AU - Khan, Afsar

N1 - RH 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.

PY - 2018/11

Y1 - 2018/11

N2 - 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.

AB - 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.

KW - 13C-1H coupling constant

KW - Quinic acid

KW - Stereoisomers

KW - Octulosonic acid

KW - Relative stabilities

KW - Density functional theory

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DO - 10.1007/s00894-018-3866-6

M3 - Article

SN - 1610-2940

VL - 24

JO - Journal of Molecular Modeling

JF - Journal of Molecular Modeling

IS - 11

M1 - 324

ER -

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

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