Abstract
A novel tandem nucleophilic displacement reaction on tetrachloropyrimidine 7 leads to molecules with two delocalized positive and one delocalized negative charge, which comprise a common π-electron system, plus one external anion. Thus, treatment of 7 with an excess of heteroaromatic nucleophiles such as 4-(dimethylamino)pyridine, 4-(pyrrolidin-1-yl)pyridine, and 1-methylimidazole, respectively, followed by the addition of water formed the tripolar bis(hetarenio)pyrimidin-4-olates 8, 9, and 10. Addition of anhydrous alcohols furnished the O-alkylated dicationic species 11−16. We contrast the spectroscopic features of the monocationic 8−10 and the dicationic 11−16 and performed a conformational study (PM3). The HOMO/LUMO profile was calculated to evaluate our classification of 8−10 as CCMB derivatives.
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