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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Degradation of three related bis(pyridinium)aldoximes in aqueous solutions at high concentrations: examples of unexpectedly rapid amide group hydrolysis.

The principal initial degradation products of two bis(pyridinium)aldoxime organophosphate-inhibited acetylcholinesterase reactivators, 1 (HI-6) and 3 (HS-6), in concentrated nonbuffered aqueous solutions approximating potential therapeutic dosage concentrations were found to be the carboxylic acid derivatives 2 and 4 formed from the hydrolysis of the amide functional group. Compounds 2 and 4 were prepared by heating 1 and 3 in the presence of high concentrations of hydroxylamine hydrochloride and characterized by 1H and 13C NMR, IR, and UV analyses. Estimates of the rates of hydrolysis of the amide groups in 1 and 3 and in model compounds 5, 7, and 8 under similar conditions were determined. The unexpectedly rapid hydrolysis of the amide groups in 1 and 3 was attributed to both the hydrogen ion catalysis of the concentrated aqueous solutions of the unusually acidic bis(pyridinium)aldoximes 1 and 3 and general acid catalysis by the aldoxime group.[1]

References

  1. Degradation of three related bis(pyridinium)aldoximes in aqueous solutions at high concentrations: examples of unexpectedly rapid amide group hydrolysis. Korte, W.D., Shih, M.L. Journal of pharmaceutical sciences. (1993) [Pubmed]
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