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Quantitative determination of mebeverine HCl by NMR chemical shift migration
Faculty
Not Specified
Year:
2009
Type of Publication:
Article
Pages:
4930-4936
Authors:
Elmasry, Manal S, Blagbrough, Ian S, Saleh, Hanaa M, Kheir, Afaf Aboul, Woodman, Timothy J
DOI:
10.1016/j.tet.2009.02.026
Journal:
TETRAHEDRON PERGAMON-ELSEVIER SCIENCE LTD
Volume:
65
Research Area:
Chemistry
ISSN
ISI:000267009400022
Keywords :
Chemical shift variation, Diffusion, (1)H NMR, Mebeverine HCl, Quantitative analysis
Abstract:
Quantitative (1)H NMR spectroscopic methods are not frequently reported, but current NMR instrumentation allows ready access to such data. Mebeverine HCl is an attractive molecule for NMR spectroscopy teaching purposes as it possesses a variety of simple but significant functional groups; we fully assign its (1)H and (13)C NMR spectra. Using mebeverine HCl, we show that concentration changes, in water as a solvent, can lead to significant changes in the (1)H chemical shifts of non-exchangeable aromatic protons and to a lesser extent to aromatic methoxy protons. An important observation is that different protons migrate to different extents as the concentration of the solute is varied, and thus the (1)H NMR spectra are concentration-dependent across a useful range. This chemical shift variation of selected protons was therefore analyzed and applied in the quantitative determination of mebeverine HCl in a medicine (Colofac IBS) formulated as a tablet. Self-association phenomena in water could account for these observed chemical shift migration effects as shown by determining the hydrodynamic radius from the modified form of the Stokes-Einstein equation, and thence the apparent hydrodynamic Volume, V(H), for mebeverine HCl in D(2)O solution which is 10-fold greater than that seen in either CDCl(3) or CD(3)OD. (C) 2009 Published by Elsevier Ltd.
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