Lomas, John S. published 《1H NMR spectra of alcohols and diols in chloroform: DFT/GIAO calculation of chemical shifts》 in 2014. The article was appeared in 《Magnetic Resonance in Chemistry》. They have made some progress in their research.Safety of 2,5-Dimethyl-2,5-hexanediol The article mentions the following:
Proton NMR shifts of aliphatic alcs. in chloroform have been computed on the basis of d. functional theory, the solvent being included by the integral-equation-formalism polarizable continuum model of Gaussian 09. Relative energies of all conformers are calculated at the Perdew, Burke and Ernzerhof (PBE)0/6-311+G(d,p) level, and NMR shifts by the gauge-including AO method with the PBE0/6-311+G(d,p) geometry and the cc-pVTZ basis set. The 208 computed CH proton NMR shifts for 34 alcs. correlate very well with the exptl. values, with a gradient of 1.00 ± 0.01 and intercept close to zero; the overall root mean square difference (RMSD) is 0.08 ppm. Shifts for CH protons of diols in chloroform are well correlated with the theor. values for (isotropic) benzene, with similar gradient and intercept (1.02 ± 0.01, -0.13 ppm), but the overall RMSD is slightly higher, 0.12 ppm. This approach generally gives slightly better results than the CHARGE model of Abraham et al. The shifts of unsaturated alcs. in benzene have been re-examined with Gaussian 09, but the overall fit for CH protons is not improved, and OH proton shifts are worse. Shifts of vinyl protons in alkenols are systematically overestimated, and the correlation of computed shifts against the exptl. data for unsaturated alcs. follows a quadratic equation. Splitting the 20 compounds studied into two sets, and applying empirical scaling based on the quadratic for the first set to the second set, gives an RMSD of 0.10 ppm. A multi-standard approach gives a similar result. Copyright © 2014 John Wiley & Sons, Ltd. The experimental procedure involved many compounds, such as 2,5-Dimethyl-2,5-hexanediol (cas: 110-03-2) .
2,5-Dimethyl-2,5-hexanediol(cas:110-03-2) on heteropoly acid catalyzed dehydration yields cyclic ethers via stereospecific intramolecular SN2 mechanism. It reacts with nitriles in concentrated sulfuric acid to yield Δ1-pyrrolines.Safety of 2,5-Dimethyl-2,5-hexanediol
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