A computational study of triazene, methyltriazene, dimethyltriazene, and trimethyltriazene is presented. A number of different conformers are analyzed and rationalized using hyperconjugation and steric interaction arguments. The transition states for rotation, inversion, and proton and methyl shifts (including water-mediated) are found and the barriers determined.Key words: triazene, ab initio, methyltriazene, 1,3-proton shift.
A computational study of a series of model triazene-based anticancer agents based on methyl- and amidyl-substituted 5-(1-triazenyl)imidazoles has been carried out, including the drugs Dacarbazine, Temozolomide, and Mitozolomide. A number of different conformers are analyzed. The transition states for the gas-phase and water-mediated triazene tautomerization reaction are found and the barriers are determined.
Reaction of diazonium salts with solutions of 1,2‐diaminocyclohexane mixed with formaldehyde affords the 1‐[2‐aryl‐1‐diazenyl]‐3‐({3‐[2‐aryl‐1‐diazenyl]perhydrobenzo[d]imidazol‐1‐yl}methyl)perhydrobenzo‐[d]imidazoles (6), a new series of bis‐triazenes with different connectivity than any previous type of bis‐triazene reported. The products have been characterized principally by NMR and IR spectroscopy, elemental analysis and unequivocally by X‐ray crystallography. The methylene protons of the perhydroimidazole rings are diastereotopic giving rise to a doublet of doublets pattern in the 1H NMR spectra. However, detailed analysis of the NMR spectra shows that there is more than one set of doublet‐of‐doublet signals, suggesting the presence of different rotameric forms of the products. The 13C NMR spectral assignments were assisted by COSY and DEPT experiments with selected compounds.
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