In this study, global reactivity descriptors such as ionization potential, electron affinity, electronegativity, chemical hardness, softness and electrophilicity index of norbornadiene derivatives which include some halogen atoms and atom groups, have been investigated with DFT/BPV86/B3LYP/B3PW91 methods with 6-31G(d,p) basis set. To determine the non-linear optical behaviours of the structures; the total dipole moment, mean polarizability and first-order hyperpolarizability values have been examined at the same theoretical level. It has been found that thiol-bonded groups in comparison with others have a much better NLO material property. In addition, the potentials being drug-active compounds of the structures have been examined with Lipinski's rule of 5 and bioactivity scores. Thiol and hydroxyl-bonded groups have a good drug-likeness and bioactivity score relative to the others.