Synthesis of a new quaternary phosphonium salt: NMR study of the conformational structure and dynamics

Oksana V Aganova; Leysan F Galiullina; Albert V Aganov; Nikita V Shtyrlin; Mikhail V Pugachev; Alexey D Strel'nik; Sergey A Koshkin; Yurii G Shtyrlin; Vladimir V Klochkov

doi:10.1002/mrc.4378

Synthesis of a new quaternary phosphonium salt: NMR study of the conformational structure and dynamics

Magn Reson Chem. 2016 Apr;54(4):320-7. doi: 10.1002/mrc.4378. Epub 2015 Dec 14.

Authors

Oksana V Aganova¹, Leysan F Galiullina¹, Albert V Aganov¹, Nikita V Shtyrlin², Mikhail V Pugachev², Alexey D Strel'nik², Sergey A Koshkin², Yurii G Shtyrlin², Vladimir V Klochkov¹

Affiliations

¹ Institute of Physics, Kazan (Volga Region) Federal University, Kremlevskaya Str., 18, 420008, Kazan, Russia.
² Research and Educational Center of Pharmacy, Kazan Federal University, Kazan, 420008, Russia.

PMID: 26661926
DOI: 10.1002/mrc.4378

Abstract

A novel phosphonium salt based on pyridoxine was synthesized. Conformational analysis of the compound in solution was performed using dynamic NMR experiments and calculations. The obtained results revealed some differences in the conformational transitions and the energy parameters of the conformational exchange of the studied compound in comparison to previously reported data for other phosphorus-containing pyridoxine derivatives. It was shown that increasing the substituent at the C-11 carbon leads to greater differences in the populations of stable states and the corresponding equilibrium energies. Copyright © 2015 John Wiley & Sons, Ltd.

Keywords: conformational transition; dynamic 1H NMR; energy barrier; nuclear Overhauser effect; quaternary phosphonium salts.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclohexanols / chemical synthesis*
Cyclohexanols / chemistry
Magnetic Resonance Spectroscopy / methods*
Models, Molecular
Quantum Theory*
Stereoisomerism

Substances

Cyclohexanols