Article ID Journal Published Year Pages File Type
1406728 Journal of Molecular Structure 2010 8 Pages PDF
Abstract

Novel disubstituted 5,5′-bi-1,2,4-triazines bearing pyridine (1), furan (2) and thiophene (3) rings at 6 and 6′-positions of the parent bitriazine were prepared as potential extractants of nuclear waste. The compounds were easily obtained by Stille coupling starting from 6,6′-bisbromo-3,3′-bis(N,N-dimethylamine)-5,5′-bi-1,2,4-triazine and the corresponding tin reagents. The molecular and crystal structures of the ligands 1–3 were determined by the X-ray analysis. The X-ray investigations show different conformations of the molecules described as gauche–gauche–gauche for 1 and gauche–cis–cis for 2 and 3. Each of the molecules resides on a twofold axis that passes through the middle of the central C5–C5′ bond. The molecular packing in 1 is influenced by the π⋯π and weak C–H⋯π interactions. The crystal structures of 2 and 3 are governed by a combination of a weak C–H⋯N hydrogen bonds and C–H⋯π interactions. Theoretical calculations using semi-empirical AM1 and DFT/B3LYP/6-311++G(d,p) ab initio methods were carried out to find correlation between conformational and electronic parameters of the molecules and their preferences to metal ions complexations.

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
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