Cucurbit[6]uril as a potential catalyst for the acidic decomposition of azidoaminoalkanes

Five azidoalkyl-1-amines and p-azidoaniline have been synthesized and complexed with cucurbit[6]uril in acidic solutions. Isothermal titration calorimetry has been employed to determine the association constant K and the enthalpy of complex formation ΔH of the azidoalkyl- and azidoarylamines. 4-Azidobutyl-1-amine forms by far the most stable complex. Cucurbit[6]uril significantly catalyzes the decomposition of the azidoalkyl- and azidoarylamines studied.