The probability of existence of a stepwise route which is in parallel with the well-known concerted pathway for the mechanism of 1,3-dipolar cycloaddition is debated by many researchers. As the route is stepwise, it would lead to emergence of at least a metastable intermediate which would produce some stereoisomers such as enantiomers and diastereomers. In 1986 the first clear stepwise example for a 1,3-dipolar cycloaddition was reported by Huisgen where an electron-poor alkene was reacted with a thiocarbonyl ylide. Since then, researchers have focused on the thiocarbonyl ylide 1,3-dipolar group in finding more stepwise examples. It was found that some reactions of a thiocarbonyl ylide with some dipolarophiles proceeded by a stepwise route, while others did not. This situation led us to investigate the probability of existence a stepwise route in parallel with the concerted path for the reaction of methyl thiocarbonyl S-oxide and C20 fullerene as a chemically active and nano-dimension electronegative alkene. To give more reliable data, Born–Oppenheimer ab initio QM/MM molecular dynamics was used.
In this study, the interactions between nitrile oxide (fulminic acid) and azide (hydrazoic acid) with the C[Formula: see text] fullerene were investigated and their priority in reacting and functionalizing surface of this fullerene were compared with each other. The results show that the 1,3-dipolar cycloaddition reaction between fulminic acid and C[Formula: see text] fullerene could occur faster than this reaction by hydrazoic acid. Therefore, nitrile oxide group as a dipole is much preferred compared to the azide functional group in reacting with the surface of C[Formula: see text] fullerene. In addition, the calculated adsorption energy and electronic density of state, DOS plots for the related species confirmed that the C[Formula: see text] fullerene can be used as sensors for sensing the hydrazoic acid and fulminic acid molecules.
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