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

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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 CDF 3 /CDClF 2 . The hydrogen bond geometries were estimated using previously established correlations linking 1 H 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 31 P NMR signal upon complexation. We show that the values of 31 P 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 31 P NMR signal by ca. 1.5 ppm to the high field.

Translated title of the contributionВлияние образования водородных связей в комплексах 1:1 фосфиновых кислот с замещенными пиридинами на 1H и 31P ЯМР химические сдвиги
Original languageEnglish
Pages (from-to)2252-2260
JournalJournal of Physical Chemistry A
Volume123
Issue number11
Early online date26 Feb 2019
DOIs
Publication statusPublished - 21 Mar 2019

Scopus subject areas

  • Physical and Theoretical Chemistry

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