Selected calculated frontier molecular orbitals (M06-2X/6-311+G(2df,2p)) for trifluoromethyl phenyl diazirine, suggesting conjugation from the aromatic ring onto the central carbon atom of the diazirine group. ring (i.e. the dihedral angle between the CF3 group, the diazirine carbon, the ipso carbon on the benzene ring, and the neighbouring ortho carbon needs to be close to zero). Achieving this conformation would require that the molecule pay a steric penalty (resulting from interactions between the CF3 group and the ortho C-H), which must be overcome by the electronic stabilization resulting from orbital delocalization.