Comparison of experimental and DFT-calculated NMR chemical shifts of 2-amino and 2-hydroxyl substituted phenyl benzimidazoles, benzoxazoles and benzothiazoles in four solvents using the IEF-PCM solvation model.

Pierens, Gregory K., Venkatachalam, T. K. and Reutens, David C. (2015) Comparison of experimental and DFT-calculated NMR chemical shifts of 2-amino and 2-hydroxyl substituted phenyl benzimidazoles, benzoxazoles and benzothiazoles in four solvents using the IEF-PCM solvation model.. Magnetic Resonance in Chemistry, 54 4: 298-307. doi:10.1002/mrc.4374


Author Pierens, Gregory K.
Venkatachalam, T. K.
Reutens, David C.
Title Comparison of experimental and DFT-calculated NMR chemical shifts of 2-amino and 2-hydroxyl substituted phenyl benzimidazoles, benzoxazoles and benzothiazoles in four solvents using the IEF-PCM solvation model.
Journal name Magnetic Resonance in Chemistry   Check publisher's open access policy
ISSN 0749-1581
1097-458X
Publication date 2015-10-09
Year available 2015
Sub-type Article (original research)
DOI 10.1002/mrc.4374
Open Access Status Not Open Access
Volume 54
Issue 4
Start page 298
End page 307
Total pages 10
Place of publication Chichester, West Sussex, United Kingdom
Publisher John Wiley and Sons
Collection year 2016
Language eng
Formatted abstract
A comparative study of experimental and calculated NMR chemical shifts of six compounds comprising 2-amino and 2-hydroxy phenyl benzoxazoles/benzothiazoles/benzimidazoles in four solvents is reported. The benzimidazoles showed interesting spectral characteristics, which are discussed. The proton and carbon chemical shifts were similar for all solvents. The largest chemical shift deviations were observed in benzene. The chemical shifts were calculated with density functional theory using a suite of four functionals and basis set combinations. The calculated chemical shifts revealed a good match to the experimentally observed values in most of the solvents. The mean absolute error was used as the primary metric. The use of an additional metric is suggested, which is based on the order of chemical shifts. The DP4 probability measures were also used to compare the experimental and calculated chemical shifts for each compound in the four solvents.
Keyword Benzothiazoles
Benzimidazoles
Benzoxazoles
Solvent effects
DFT calculations
Chemical Shifts
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2016 Collection
Centre for Advanced Imaging Publications
 
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Created: Sat, 07 Nov 2015, 01:43:13 EST by Lorine Wilkinson on behalf of Centre for Advanced Imaging