A DFT computational study of the molecular mechanism of [3 + 2] cycloaddition reactions between nitroethene and benzonitrile N-oxides

Radomir Jasiński; Ewa Jasińska; Ewa Dresler

doi:10.1007/s00894-016-3185-8

A DFT computational study of the molecular mechanism of [3 + 2] cycloaddition reactions between nitroethene and benzonitrile N-oxides

J Mol Model. 2017 Jan;23(1):13. doi: 10.1007/s00894-016-3185-8. Epub 2016 Dec 28.

Authors

Radomir Jasiński¹, Ewa Jasińska², Ewa Dresler³

Affiliations

¹ Institute of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155, Kraków, Poland. radomir@chemia.pk.edu.pl.
² Institute of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155, Kraków, Poland.
³ Institute of Heavy Organic Synthesis "Blachownia", Energetyków 9, 47-225, Kędzierzyn-Koźle, Poland.

Abstract

DFT calculations were performed to shed light on the molecular mechanism of [3 + 2] cycloadditions of simple conjugated nitroalkenes to benzonitrile N-oxides. In particular, it was found that these processes proceed by a one-step mechanism through asynchronous transition states. According to the latest terminology, they should be considered polar but not stepwise processes.

Keywords: DFT study; Mechanism; Nitrile N-oxides; Nitroalkenes; [3 + 2] cycloaddition.