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1 H NMR spectra of ethane‐1,2‐diol and other vicinal diols in benzene: GIAO/DFT shift calculations
Author(s) -
Lomas John S.
Publication year - 2013
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.3899
Subject(s) - chemistry , vicinal , diol , benzene , carbon 13 nmr , nmr spectra database , nuclear magnetic resonance spectroscopy , computational chemistry , benzene derivatives , spectral line , organic chemistry , chemical synthesis , physics , astronomy , biochemistry , in vitro
The proton NMR spectra of several 1,2‐diols in benzene have been analysed so as to associate each magnetically nonequivalent proton with its chemical shift. The shifts and coupling constants of the OH and methylene protons of ethane‐1,2‐diol have been determined in a wide range of solvents. The conformer distribution and the proton NMR shifts of these 1,2‐diols in benzene have been computed on the basis of density functional theory. The solvent is included using the integral–equation–formalism polarizable continuum model implemented in Gaussian 09. Relative Gibbs energies for all stable conformers are calculated at the Perdew, Burke and Enzerhof (PBE)0/6‐311 + G(d,p) level, and shifts are calculated using the gauge‐including atomic orbital method with the PBE0/6‐311 + G(d,p) geometry but using the cc‐pVTZ basis set. Previous calculations on ethane‐1,2‐diol and propane‐1,2‐diol have been corrected and extended. New calculations on tert ‐butylethane‐1,2‐diol, phenylethane‐1,2‐diol, butane‐2,3‐diols ( dl and meso ) and cyclohexane‐1,2‐diols ( cis and trans ) are presented. Overall, the computed NMR shifts are in good agreement with experimental values for the OH protons but remain systematically high for CH protons. Some results based on the Gaussian 03 solvation model are included for comparison. Copyright © 2012 John Wiley & Sons, Ltd.