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Differential protonation and dynamic structure of doxylamine succinate in solution using 1H and 13C NMR

✍ Scribed by B. S. Somashekar; G. A. Nagana Gowda; A. R. Ramesha; C. L. Khetrapal

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
129 KB
Volume
42
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

A protonation and dynamic structural study of doxylamine succinate, a 1:1 salt of succinic acid with dimethyl‐[2‐(1‐phenyl‐1‐pyridin‐2‐yl‐ethoxy)ethyl]amine, in solution using one‐ and two‐dimensional ^1^H and ^13^C NMR experiments at variable temperature and concentration is presented. The two acidic protons of the salt doxylamine succinate are in ‘intermediate’ exchange at room temperature, as evidenced by the appearance of a broad signal. This signal evolves into two distinct signals below about −30 °C. A two‐dimensional ^1^H^1^H double quantum filtered correlation experiment carried out at −55 °C shows protonation of one of the acidic protons to the dimethylamine nitrogen. A two‐dimensional rotating frame ^1^H^1^H NOE experiment at the same temperature reveals that the other proton remains with the succinate moiety. Comparison of the ^1^H and ^13^C chemical shifts and the ^13^C T~1~ relaxation times of the salt with those of the free base further substantiate the findings. Copyright © 2004 John Wiley & Sons, Ltd.

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