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Crossed Beam Experiments and Computational Studies of Pathways to the Preparation of Singlet Ethynylsilylene (HCCSiH; X1A'): The Silacarbene Counterpart of Triplet Propargylene (HCCCH; X3B).

Ethynylsilylene (HCCSiH; X1A') has been prepared in the gas phase through the elementary reaction of singlet dicarbon (C2) with silane (SiH4) under single-collision conditions. Electronic structure calculations reveal a barrierless reaction pathway involving 1,1-insertion of dicarbon into one of the silicon-hydrogen bonds followed by hydrogen migration to form the 3-sila-methylacetylene (HCCSiH3) intermediate. The intermediate undergoes unimolecular decomposition through molecular hydrogen loss to ethynylsilylene (HCCSiH; Cs; X1A'). The dicarbon-silane system defines a benchmark to explore the consequence of a single collision between the simplest "only carbon" molecule (dicarbon) with the prototype of a closed-shell silicon hydride (silane) yielding a nonclassical silacarbene, whose molecular geometry and electronic structure are quite distinct from the isovalent triplet propargylene (HCCCH; C2; 3B) carbon-counterpart. These organosilicon transients cannot be prepared through traditional organic, synthetic methods, thus opening up a versatile path to access the previously largely elusive class of silacarbenes.