I am looking for a technique that I could use to see and measure the energy of these interactions. The problem is that is an electronic interaction between the orbitals of the two groups. I thought about NMR, or more sophisticated techniques as XANES/EXAFS, but I am not sure. Do you have any idea?
IR, UV-vis and NMR could tell you about the interaction that would have taken place. But is it that you are looking for or is it quantitative determination?
I'm biased, but NMR could certainly be a useful tool -- the long-range J-couplings in aromatics in particular are very sensitive to changes in electronic structure. You would probably need to add in DFT calculations for quantitative interpretation, which is certainly feasible for small molecules (possible, but more challenging, for larger molecules).
We wrote a paper about measuring J-couplings in aromatics using zero-field NMR (attached), though it's not yet a common technique. Still, conventional high-resolution NMR should permit reasonably precise measurement of J-coupling values.
Article High-Resolution Zero-Field NMR J-Spectroscopy of Aromatic Compounds
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