A combined experimental and density functional theory investigation of the reaction between β-Nitrostyrene and trimethylsilyl cyanide

In this study, a reaction between β-nitrostyrene and trimethylsilyl cyanide was examined using both experimental and computational approaches. The reaction was carried out using 2 eq TMSCN in 3 mL methanol, with 10 mol% NH 4 F as the catalyst. The resulting product mixture was analyzed by gas chromatography–mass spectrometry, which indicated that cinnamilnitrile was formed as the major product. For the computational investigation, energy profiles of plausible reaction pathways were evaluated at the M06-2×/def2TZVP level of theory. Four reaction pathways were considered, leading respectively to the formation of cinnamilnitrile, β-nitrosostyrene, 2-cyano-2-phenylacetaldehyde, and α-cyano-β-nitrosostyrene. The calculated energy profiles indicated that the pathway leading to cinnamilnitrile is the most favorable, consistent with the experimental observations. Additionally, the NBO charge analysis and reactivity parameters further supported the mechanistic preference for this pathway.