Computational Description of a Huisgen Cycloaddition Inside a Self-Assembled Nanocapsule

Density functional theory calculations are applied to the study of a cycloaddition reaction between phenyl acetylene and phenyl azide taking place inside a self-assembled nanoreactor derived from the coupling of two resorcinarene-derived units. Calculations are applied to all steps in the reactivity of the system: self-assembly, guest trapping, guest exchange, in-core reaction, and product release. A reaction network is built, and the evolution of concentrations of a large variety of species over a range of time scales is obtained through the application of a kinetic model. The modeled behavior of the nanocapsule and its guests reproduces the experimental observations and completes our knowledge and understanding of this chemical system.