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Stereochemical study of tolperisone, a muscle relaxant agent, by circular dichroism and ultraviolet spectroscopy
Author(s) -
Zsila Ferenc,
Hollósi Miklós,
Gergely András
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/1520-636x(2000)12:10<720::aid-chir4>3.0.co;2-2
Subject(s) - chemistry , circular dichroism , chromophore , chirality (physics) , stereochemistry , absolute configuration , hydrochloride , moiety , vibrational circular dichroism , cotton effect , helicity , conformational isomerism , enantiomer , ketone , crystallography , photochemistry , organic chemistry , chiral symmetry , molecule , particle physics , physics , quantum mechanics , nambu–jona lasinio model , quark
The stereochemistry of tolperisone, a chiral aryl‐alkyl basic ketone was investigated by means of circular dichroism (CD) and ultraviolet (UV) spectroscopy. The unusually high optical activity of tolperisone hydrochloride in the n→π* region is interpreted by the presence of a chiral conformer in solution. For stereochemical reasons, the C = O group and the aromatic moiety lack coplanarity by forming an inherently dissymetric chromophore, of M helicity. Similar helicity prevails in the crystal phase, according to the solid‐state CD spectrum of (−)‐tolperisone HCl salt. The chirality rule proposed by Snatzke for nonplanar benzoyl chromophores predicts the absolute configuration of (−)‐tolperisone hydrochloride to be R , in agreement with other α‐methyl‐β‐amino‐ketones. Chirality 12:720–726, 2000. © 2000 Wiley‐Liss, Inc.