A molecular mechanism of the [3+2] cycloaddition has been explored using various DFT theoretical levels. | A DFT computational study on the 3 2 cycloaddition between parent thionitrone and nitroethene Current Chemistry Letters 7 2018 27 34 Contents lists available at GrowingScience Current Chemistry Letters homepage A DFT computational study on the 3 2 cycloaddition between parent thionitrone and nitroethene Karolina Kula and Agnieszka Łapczuk-Krygier Cracow University of Technology Institute of Organic Chemistry and Technology Warszawska 24 31-155 Cracow Poland CHRONICLE ABSTRACT Article history A molecular mechanism of the 3 2 cycloaddition has been explored using various DFT Received December 22 2017 theoretical levels. It was found that the reaction proceeds via transition states with different Received in revised form synchronicity but no intervention of the theoretical possible zwitterionic intermediates. January 29 2018 Additionally regioselectivity of the cycloaddition process has been analysed using vibrational Accepted February 15 2018 analysis of localised TSs. Available online February 15 2018 Keywords Thionitrone Nitroethene Nitroisothiazolidine 3 2 cycloaddition DFT study 2018 Growing Science Ltd. All rights reserved. 1. Introduction Five-membered heterocycles are widely used as biologically active Heterocyclic compounds with two different heteroatoms particularly are the object of growing research interest of chemists. In particular compounds bearing the thiazole ring in the molecular structure such as isothiazolidines or isothiazolines have antitumor anti-allergic anti-diabetic anti-inflammatory anthelmintic and anti-HIV The isothiazole ring is present in compounds with biological activity such as the pharmaceutical drugs ziprasidone and 12 Subsequently it should be noted that the presence of nitro-group in the organic molecule generally stimulates additive functions of Furthermore nitro-group is an exceedingly attractive starting point for further transformation into .
