The noncovalent interactions of the CH3 center dot, Cl-center dot, CF3 center dot, and C(CH3)(3)(center dot) radicals with CF3X molecules (X = Cl, Br, I) have been investigated using CCSD(T)/aug-cc-pVTZ energy calculations on MP2/aug-cc-pVTZ-optimized geometries. The electrophilic chlorine atom prefers to complex with the equatorial belt of the heavier halogen X, whereas the nucleophilic radicals CH3 center dot and C(CH3)(3)(center dot) coordinate preferentially with the sigma-hole of X to give C-3v complexes. Complexation energies are generally small, ranging up to 5 kcal mol(-1) for CF3I with either the chlorine atom or the Bu-t radical. Within the continuum from pure one-electron (SOMOLUMO) to pure three-electron (SOMO-HOMO) bonds, the results can be interpreted in terms of predominantly one-electron bonds for nucleophilic radicals but closer to three-electron bonds for the chlorine atom. The trifluoromethyl radical binds very weakly via interhalogen interactions; the carbon radical center plays no role in the bonding.