Intermolecular interactions between benzene and 1,3,5-triazine: a new tool for crystal engineering and molecular recognition

Intermolecular interactions between the electron-rich surface of benzene and the electron-poor surface of 1,3,5-triazine in many selected reciprocal orientations have been investigated by ab initio calculations at the HF and MP2 levels using the 6-311G**, 6-311++G** and 6-311++G(3df,p) basis sets. Minimum energy structures, binding energies and charge transfer between monomers have been calculated. The highest binding energies occur in parallel structures. These intermolecular interaction modes between benzene and 1,3,5-triazine can be exploited as a new non-covalent design principle for molecular recognition and crystal engineering and have been used for the design of a new receptor for supramolecular recognition of benzene in the gas-phase.