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- Title
Permethylated Salts and Radicals Derived from Azo peri-Naphthalenes.
- Authors
Bohle, D. Scott; Chua, Zhijie; Johnstone, Timothy; Moiseev, Andrey G.; Perepichka, Inna; Rosadiuk, Kristopher A.
- Abstract
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 1 H-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.
- Subjects
NAPHTHALENESULFONIC acids; TRIAZENES; RADICALS; X-ray crystallography; ALKYLATION; RAMAN spectroscopy
- Publication
ChemPlusChem, 2012, Vol 77, Issue 5, p387
- ISSN
2192-6506
- Publication type
Article
- DOI
10.1002/cplu.201200021