The conformations of dicyclopropyl, isopropyl cyclopropyl, and diisopropylcarbenes were optimized using density functional theory (B3LYP/6-31G(d)). We showed that the optimized geometries of carbenes with cyclopropyl groups are fully in accord with those expected for bisected W-shaped conformations, in which the effective hyperconjugation of a cyclopropyl group with singlet carbene can occur. The stabilization energies were evaluated at the B3LYP/6-311+G(3df, 2p)//B3LYP/6-31G(d) + ZPE level using an isodesmic equation. The relative stability of carbenes is in the order $(c-Pr)_2$C: > (i-Pr)(c-Pr)C: > $(i-Pr)_2$C:, and a cyclopropyl group stabilizes carbene more than an isopropyl group by nearly 9 kcal/mol. Energies for the decomposition of diazo compounds to carbenes increase in the order $(c-Pr)_2$ < (i-Pr)(c-Pr) < $(i-Pr)_2$ by ~9 kcal/mol each. From a singlettriplet energy gap ($E_{ST}$) calculation, the singlet level is lower than the triplet level and the $E_{ST}$ shows a trend similar to the stabilization energy calculations. For comparison, the optimized geometries and stabilization energies for the corresponding carbocations were also studied at the same level of calculation. The greater changes in geometries and the higher stabilization energies for carbocations compared to carbenes can explain the greater hyperconjugation effect.