| Popis: |
By careful choice of reaction conditions 1-methylnaphtho[1,8-de]-1,2,3-triazine and 1,3-dimethylnaphtho[1,8-de]-1,2,3-triazinium triflate are readily prepared by the alkylation of 1H-naphtho[1,8-de]-1,2,3-triazine. The electronic spectra for these bathochromically shifted dyes are reported for a range of solvents as are their vibrational spectra and theoretical structures from density functional theory, B3LYP/6-311++G**. The 15N substitution into the middle nitrogen atom allows for the identification of strong azine bands in the IR and Raman spectra as well as in the 15N NMR spectrum. X-ray crystallography is used to characterize the solid-state structures of two of these new triazine derivatives and these structures are used to benchmark the theoretical and spectroscopic discussions. The corresponding 1,3-dimethyltriazinium radical is prepared and characterized by cyclic voltammetry, spectroelectrochemistry, and EPR spectroscopy. Unlike the related transient 1,2,4-triazene radicals, the 1,3-dimethyl-1,2,3-naphthotriazyl radical is markedly more stable. |
