Unravelling the Unexpected: Mechanistic Insights and DFT Studies on the Formation of Azine from N-Acylhydrazones.

Autor: Abdulwahab, M. K., Tang, W. K., Yehye, W. A., Ariffin, A.
Předmět:
Zdroj: Russian Journal of General Chemistry; Apr2024, Vol. 94 Issue 4, p969-977, 9p
Abstrakt: Acylydrazone is the common product of the reaction between hydrazide and aldehyde. However, in our previous study, azine was unexpectedly synthesized from the reaction between hydrazide and aldehyde, instead of acylhydrazone. Coincidentally, plenty of reports also obtained azines unexpectedly in reactions involving hydrazides and hydrazones, albeit unable to provide satisfying explanations for the observation. To shed light on this occurrence, we designed and executed several experiments to understand the mechanism for the formation of azine. Based on the results, acylhydrazones were suggested as the intermediates during the conversion to azines, and the acidic condition catalyzed the reaction. The requirement of acidic condition was further supported by density functional theory (DFT) calculations. Additionally, the presence of water was observed as the main cause of the conversion of acylhydrazones to azine in the absence of aldehyde. The results caution future works on the usage of harsh conditions and moisture in the reactions involving hydrazide, hydrazone and azine. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index