Ab initio calculations are reported on 7-azaindole and the 1:1 complexes between 7-azaindole and water and methanol. Geometry optimizations using restricted Hartree-Fock wavefunctions and a double zeta plus polarization basis set were performed on the tautomeric minima and the transition states connecting these minima. Energetics were predicted using second-order perturbation theory. The ground state activation energy for tautomerization is predicted to decrease from nearly 60 kcal/mol in 7-azaindole to about 20 kcal/mol for the 1:1 complexes. Vertical excitation of the 1:1 complex with water, qualitatively estimated using singly excited configuration interaction, is predicted to reverse the order of stability of the two tautomers.