Determination of tautomeric preference of fenobam in solution by high-resolution NMR spectroscopy

Xuming Sha; Shaodong Chen; Xiaojing Zheng; Xin Ye; Hailu Zhang; Shaohua Huang

doi:10.1002/mrc.5127

Determination of tautomeric preference of fenobam in solution by high-resolution NMR spectroscopy

Magn Reson Chem. 2021 Jun;59(6):641-647. doi: 10.1002/mrc.5127. Epub 2021 Jan 14.

Authors

Xuming Sha¹, Shaodong Chen², Xiaojing Zheng¹, Xin Ye², Hailu Zhang², Shaohua Huang^{1

3}

Affiliations

¹ Institute of Drug Discovery Technology, Ningbo University, Ningbo, China.
² Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, Suzhou, China.
³ Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences, Ningbo University, Ningbo, China.

PMID: 33368586
DOI: 10.1002/mrc.5127

Abstract

In this work, tautomeric preference of fenobam in solution was investigated by homonuclear and heteronuclear solution nuclear magnetic resonance (NMR) spectroscopy. ¹ H-¹ H nuclear Overhauser effect spectroscopy (NOESY) spectrum revealed that fenobam in liquid state exists exclusively in one of the two possible tautomeric structures, which was confirmed by ¹ H-¹³ C HSQC and heteronuclear multiple bond correlation (HMBC) spectra. Moreover, difference between the two tautomeric structures was studied by theoretical calculations, which further proved the result obtained by the NMR experiments.

Keywords: 13C; 1H; NMR Spectroscopy; NOESY; fenobam; tautomer; theoretical calculation.

Publication types

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

Abstract

Publication types

Grants and funding