A ¹⁵N labeled nitroxide derivative containing a benzophenone chromophore was incarcerated into an octaacid nanocapsule, which was confirmed by ¹H NMR and EPR spectroscopy.  Electron spin-spin superexchange between the ¹⁵N labeled incarcerated nitroxide and a ¹⁴N labeled free nitroxide in the external aqueous solution was observed by EPR spectroscopy. The observation of spin-spin coupling, through the walls of the carcerand is reflected in the simultaneous line-broadening of both the ¹⁵N labeled and ¹⁴N labeled nitroxides. The computer-assisted analysis of the EPR data further provides direct information on the motion and the polarity of both the incarcerated paramagnetic nitroxide and the nitroxides in the external bulk aqueous phase. We also show how communication between an incarcerated guest and molecules in the bulk solvent can be enhanced or inhibited by supramolecular factors such as Columbic attraction or repulsion between a charged guest@host complex (incarcerated ¹⁵N nitroxide) and charged molecules in the aqueous phase. In addition, time resolved EPR experiments were performed, where incarcerated ¹⁵N nitroxide labeled benzophenone was excited by laser pulses to generate spin polarized ¹⁵N nitroxides.  The spin polarization of the incarcerated ¹⁵N nitroxide was transferred to a ¹⁴N labeled free nitroxide in the external solution.