| المؤلفون: |
Vaddypally S; Department of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, Pennsylvania 19122, United States., Byrne AN; Department of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, Pennsylvania 19122, United States., Goldsmith CF; School of Engineering, Brown University, 184 Hope Street, Providence, Rhode Island 02912, United States., Zdilla MJ; Department of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, Pennsylvania 19122, United States., Kiselev VG; School of Engineering, Brown University, 184 Hope Street, Providence, Rhode Island 02912, United States.; Novosibirsk State University, 1 Pirogova Street, 630090 Novosibirsk, Russia.; Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences, 3 Institutskaya Street, 630090 Novosibirsk, Russia.; Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, 4 Kosygina Street, 119991 Moscow, Russia. |
| مستخلص: |
Crystallization of the reaction mixture of 2-amino-4,6-diazido-1,3,5-triazine and excess tert -butylamine results in the isolation of tert -butylammonium N , N -[1' H -(1,5'-bitetrazol)-5-yl]cyanamidate, suggesting a complex decyclization/cyclization rearrangement involving breakage of the six-membered aromatic ring and the formation of two new five-membered azole rings mediated by deprotonation of the precursor by the amine. The addition of tert -butylamine to 2-amino-4,6-diazido-1,3,5-triazine gives spectroscopic indication of thermodynamically unfavorable reactivity in low-dielectric solvents, and high-level quantum chemical computations also suggest its formation to be unfavorable. A computed interconversion pathway describes the likely reaction mechanism and supports the general thermodynamic unfavorability of the reaction and the requirement for a high-dielectric environment to template formation of the ionic product and its trapping by crystallization. |
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