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Vibrational spectroscopic characterisation of two antidotes of the bis-pyridinium-4-aldoxime type and their complexes with the aquapentacyanoferrate(II) ion

1, 1’ -Bis(pyridinium-4-aldoxime)oxydimethylene dichloride (Toxogonin) and 1, 1’ -bis(pyridinium-4-aldoxime)trimethylene dibromide (TMB-4) are known to be acetylcholinesterase reactivators and effective antidotes in intoxication with organophosphates. Toxogonin has been proved to be less toxic and it is used therapeutically in insecticide poisonings in many European countries. Despite their chemical and structural resemblance, considerable differences concerning the Ka1/ Ka2 ratios of their oxime groups [1] and consequently their reactivity toward the phosphorylated enzyme [2] as well as to the aquapentacyanoferrate(II) ion were established. In order to give more insight into the correlation between chemical structure, reactivity and biological function of Toxogonin and TMB-4, we undertook a comparative FT-IR and FT-Raman spectroscopic study of these compounds and their pentacyanoferrate(II) complexes. The complexes were synthesized and isolated as solids by known procedures [3]. The analysis is focused to determination of the possible differences in conformational and structural features of these compounds as well as of the mode of their coordination to the iron(II) centre. References 1.B. Foretić and N. Burger, Monatsh. Chem. 135 (2004), 261– 267. 2.K. Schoene and E. M. Strake, Biochem. Pharmacol. 20 (1971), 1041– 1051. 3.N. Burger and V. Hankonyi, Polyhedron 5 (1986), 663– 665.

1; 1’ -bis(pyridinium-4-aldoxime)trimethylene dibromide; 1; 1’ -Bis(pyridinium-4-aldoxime)oxydimethylene dichloride; Vibrational spectra

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