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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
Author(s) -
Pierens Gregory K.,
Venkatachalam T. K.,
Reutens David C.
Publication year - 2016
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.4374
Subject(s) - chemical shift , chemistry , solvation , benzene , computational chemistry , proton nmr , carbon 13 nmr , density functional theory , solvent , organic chemistry
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. Copyright © 2015 John Wiley & Sons, Ltd.