A unified semi-classical theory applicable to ion-polar molecule reaction kinetics and electron-dipole spectroscopy is presented within a planar ion/point-dipole model. The forms of the trapped periodic orbits that constitute dividing surfaces between internal and external regions of phase space are determined and their properties are shown to be well represented by a semianalytical adiabatic theory. Subsequent applications of the adiabatic theory to electron-dipole dynamics (a) yield a good approximation to the critical dipole for electron capture and (b) predict an exponential gap law for the excited states of electron/fixed dipole states, in good agreement with recent ab initio calculations. Extension of the theory to include dipoles of finite length, d, provides a correlation of the critical strength with d/I 1/2 where I is the molecular moment of inertia.