Affiliations: [a]
College of Biological Science and Technology, University of Jinan, Jinan, Shandong, People’s Republic of China | [b]
School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, People’s Republic of China
Correspondence:
[*]
Corresponding author: Xiaojun Tan, College of Biological Science and Technology, University of Jinan, Jinan,
Shandong, 250022, People’s Republic of China. Tel./Fax: +86 531 82767363; E-mail: [email protected].
Abstract: The cycloaddition reaction mechanism between interstellar molecules ketenimine and acetonitrile has been systematically investigated employing the second-order Møller-Plesset perturbation theory method in order to better understand the reactivity of heterocumulene ketenimine with acetonitrile. Geometry optimizations and vibrational analyses have been performed for the stationary points on the potential energy surfaces of the system. Calculations show that five-membered cyclic carbene intermediates could be afforded through pericyclic reaction processes between ketenimine and acetonitrile. Through the following intramolecular H-transfer processes, carbene intermediates can be isomerized to the corresponding 2-methylimidazole and 3-methylpyrazole derivatives, respectively. In addition, imidazole and pyrazole compounds can be produced through the intermolecular H-transfer processes on the basis of the formed cyclic carbene intermediates. The present study is helpful to understand the formation of prebiotic species in interstellar space.
