140133-82-0Relevant academic research and scientific papers
Synthesis and X-Ray Structure of 3,3'-Dimethyl-5,5'-diphenyl-4,4'-bi-4H-1,2,4-triazole
Carlsen, Per H. J.,Iversen, Erik H.,Samuelsen, Emil J.,Helgesson, Goeran,Jagner, Susan
, p. 200 - 204 (2007/10/02)
The sterically hindered N,N'-linked bitriazole, 3,3'-dimethyl-5,5'-diphenyl-4,4'-bi-4H-1,2,4-triazole, has been prepared by reaction of 4-amino-3,5-dimethyl-4H-1,2,4-triazole with bis(α-chlorobenzyliden)hydrazine in refluxing xylene.The product was an unexpected isomer of the bitriazole.A mechanism for its formation is proposed.An X-ray structure analysis of the product revealed that the triazole rings are close to perpendicular, 73 deg, and the phenyl rings are also twisted by large angles (60 and 35 deg) out of the heterocyclic planes.Connectting bonds between the phenyl and triazole rings are long, close to single bonds, 1.40(4) and 1.472(5) Angstroem, respectively., indicating reduced ?-cunjugation between the rings.The N-N' bond is somewhat shorter than an N-N single bond, suggesting some attraction between the triazole rings.The N1-N2 bonds in the triazoles are noticeably longer than observed in phenyl substituted triazoles.The crystal is monoclinic and belongs to space group P21/n with a = 9.072, b = 11.393, c = 15.698 Angstroem, β = 96.60 deg, Z = 4 and R = 0.050 for 217 parameters and 1686 observed reflections.
