Reactions of laser-ablated silicon atoms with di-, tri-, and tetrahalomethanes in excess argon were investigated, and the products were identified from the matrix infrared spectra, isotopic shifts, and density functional theory energy, bond length, and frequency calculations. Dihalomethanes produce planar singlet silenes (CH2=SiX2), and tri- and tetrahalomethanes form triplet halosilyl carbenes (HC-SiX3 and XC-SiX3). The Si-bearing molecules identified are the most stable, lowest-energy product in the reaction systems. While the C-Si bond in the silene is a true double bond, the C-Si bond in the carbene is a shortened single bond enhanced by hyperconjugation of the two unpaired electrons on C to sigma*(Si-X) orbitals, which contributes stabilization through a small amount of pi-bonding and reduction of the HCSi or XCSi angles. The C-Si bond lengths in these carbenes (1.782 angstrom for HC-SiF3) are between the single-bond length in the unobserved first insertion intermediate (1.975 angstrom for CHF2-SiF) and the double-bond length in the silene (1.704 angstrom for CHF=SiF2). The silicon s(2)p(2) and titanium s(2)d(2) electron configurations produce similar primary products, but the methylidyne with Ti has a bond to carbon stronger than that of the halosilyl carbene.