N,N-Diethyl-2-hydroxyethanaminium 2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate dihydrate

Abstract

In the title mol­ecular salt, C6H16NO+·C10H4N5O9 −·2H2O, which crystallizes as a dihydrate, O—H⋯O hydrogen bonds link the barbiturate anion, the ethanaminium cation and the water mol­ecules of crystallization. The dihedral angle between the rings in the anion is 43.71 (8)°. In the crystal, an R 2 2(8) ring motif hydrogen-bonding pattern is also found involving inversion-related barbiturate rings with N—H⋯O hydrogen bonds. As a result of the various hydrogen bonds an infinite two-dimensional network, propagating in (10), is formed.

2-Methylpyridinium 5-(2,4-dinitrophenyl)-1,3-dimethylbarbiturate

“…Good crystallinity of the title compound prompted us to undertake single-crystal X-ray studies. The bond lengths and bond angles of the barbiturate residue of the molecular salt reported in the present article are compatible with those of related barbiturates synthesized in our laboratory earlier (Kalaivani & Malarvizhi, 2009;Kalaivani & Buvaneswari, 2010;Buvaneswari & Kalaivani, 2011). The structure of the molecular salt of the present work is shown in scheme 1.…”

N,N-Diethylanilinium 2,4-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,4-tetrahydropyrimidin-6-olate

“…In the present investigation, it forms a different type of molecular salt (scheme) with the electron-deficient nitro aromatic compound, 1-chloro-2,4,6-trinitrobenzene (picryl chloride) in the presence of barbituric acid. We have already reported molecular salts of a similar type obtained from chlorine containing nitro aromatic compounds, barbituric acid and aliphatic amines (Kalaivani et al, 2008, Kalaivani & Malarvizhi, 2009, Kalaivani & Buvaneswari, 2010, Buvaneswari & Kalaivani, 2011. As noticed in other barbiturates, ring motifs are observed in the crystal structure of the title molecule.…”

N,N-Diethylanilinium 5-(2,4-dinitrophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate

“…The methylene group of barbituric acid [a pyrimidine derivative] is flanked on both sides by the electron-withdrawing carbonyl groups which makes the hydrogen atoms highly acidic. These acidic H atoms have been targeted by our group in the preparation of a number of extraordinarily stable barbiturates (Kalaivani & Malarvizhi, 2009;Buvaneswari & Kalaivani, 2011a;Kalaivani et al, 2012;Babykala & Kalaivani, 2012). We have reported on the crystal structure of a barbiturate related to the title molecular salt but derived from 1-chloro-2,4,6-trinitrobenzene (TNCB) and barbituric acid in the presence of N,N-diethylaniline (I) (Buvaneswari & Kalaivani, 2011b).…”