Crystal and Molecular Structure, and Spectral Characteristics of Sodium 3,5-Bis(Hydroxyimino)-1-Methyl-2,4,6-Trioxocyclohexanide

• DOI: 10.4236/csta.2012.13009
• Publication Date: 2012-12-25T22:45:45Z
• Authors: Olga Kovalchukova; Nguyen Dinh Do; Adam Stash; Vitaly Bel’sky; Paul Strashnov; Andrew Alafinov; Oleg Volyansky; Svetlana Strashnova; Konstantin Kobrakov
• Keywords: 01 natural sciences; 0104 chemical sciences

Sodium 3,5-bis(hydroxyimino)-1-methyl-2,4,6-trioxocyclohexanide C7H5N2NaO5 (I) has been isolated as the only product of the reaction of nitrosation of methylphloroglucinol. The structure of the titled compound has been determined from single crystal X-ray diffraction data. The hydrated C7H5N2NaO52.5H2O crystallizes in the monoclinic space group C2/c, with a(?) 16.408(3); b(?) 12.446(3); c(?) 13.716(3); (o) 126.34(3). The planar organic anion exists in a triketo-dihydroxyimino form with the C–O and C–N distances from 1.220(2) to 1.271(2) ? and from 1.292(2) to 1.293 ? respectively. In the IR spectrum of I, the sharp absorption band occurred at 1681 cm-1 due to C=O stretching indicating the strong H-interactions. The correlations of theoretical (DFT-B3LYP/aug-cc-pVDZ) and experimental UV-vis absorption spectra in neutral and alkaline ethanolic solutions showed the existence of hydroxyimino-nitroso tautomerism while ionization of I.