化学
脱质子化
三嗪
戒指(化学)
结晶
反应性(心理学)
丁胺
药物化学
胺气处理
立体化学
高分子化学
有机化学
医学
病理
离子
替代医学
作者
Shivaiah Vaddypally,Alex N. Byrne,C. Franklin Goldsmith,Michael J. Zdilla,Vitaly G. Kiselev
标识
DOI:10.1021/acs.inorgchem.3c04338
摘要
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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