@article{409, keywords = {Absolute configuration, Chiral conformer, Circular dichroism and ultraviolet spectroscopy, Dipole-dipole interaction, Nonplanar benzoyl chromophore, Tolperisone}, author = {Ferenc Zsila and M. Hollósi and András Gergely}, title = {Stereochemical study of tolperisone, a muscle relaxant agent, by circular dichroism and ultraviolet spectroscopy}, abstract = {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. (C) 2000 Wiley-Liss, Inc.}, year = {2000}, journal = {Chirality}, volume = {12}, pages = {720-726}, month = {2000}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-0033783686&partnerID=40&md5=073420698572b56b6cfa4cfe4ae1638f}, note = {Cited By :10Export Date: 25 February 2016}, }