Influence of Hydrogen Bonds in 1:1 Complexes of Phosphinic Acids with Substituted Pyridines on 1 H and 31 P NMR Chemical Shifts

The Journal of Physical Chemistry. a
I S GibaPeter M Tolstoy

Abstract

Two series of 1:1 complexes with strong OHN hydrogen bonds formed by dimethylphosphinic and phenylphosphinic acids with 10 substituted pyridines were studied experimentally by liquid state NMR spectroscopy at 100 K in solution in a low-freezing polar aprotic solvent mixture CDF3/CDClF2. The hydrogen bond geometries were estimated using previously established correlations linking 1H NMR chemical shifts of bridging protons with the O···H and H···N interatomic distances. A new correlation is proposed allowing one to estimate the interatomic distance within the OHN bridge from the displacement of 31P NMR signal upon complexation. We show that the values of 31P NMR chemical shifts are affected by an additional CH···O hydrogen bond formed between the P═O group of the acid and ortho-CH proton of the substituted pyridines. Breaking of this bond in the case of 2,6-disubstituted bases shifts the 31P NMR signal by ca. 1.5 ppm to the high field.

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Citations

Mar 25, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alexei S Ostras'Peter M Tolstoy
Nov 15, 2020·The Journal of Chemical Physics·Ilya G Shenderovich
Apr 22, 2021·The Journal of Organic Chemistry·Mira MilicAnnaliese K Franz

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