Abstract: Density functional theory (DFT) calculation,at the B3LYP/6-311G(d,p) level of theory,were performed to investigate the mechanism,potential energy surface,substituent effect and solvent effect of hetero-Diels-Alder reactions of 2-silanaphthalenes with acetylene and phenylacetylene and the title reactions were compared with those involving silabenzenes.The results show that all of studied reactions proceed in a concerted but nonsynchronous way.The influences of phenyl at C atom of acetylene on activation barrier of reaction were determined by relative position of phenyl with respect to Si atom in products.The influences of C(CH3)3 or NH2 groups at Si atom of 2-silanaphthalene on the potential energy surface are trivial,however,the influence of CCl3 group is complex.Benzene as a solvent has only trivial influence on the potential energy surface of the studied reactions.The hetero-Diels-Alder reactions of 2-silanaphthalenes with acetylene and phenylacetylene take place more difficultly tha...更多