Example：10.1021/acsami.1c06204 or Chem. Rev., 2007, 107, 2411-2502
Phenol and Toluene Stacking Interactions, Including Interactions at Large Horizontal Displacements. Study of Crystal Structures and Calculation of Potential Energy Surfaces Crystal Growth & Design (IF4.076), Pub Date : 2020-01-13, DOI: 10.1021/acs.cgd.9b01353 Jelena M. Živković, Ivana M. Stanković, Dragan B. Ninković, Snežana D. Zarić
The study of crystal structures from the Cambridge Structural Database (CSD) shows that most of p-phenol/p-phenol and toluene/toluene stacking interactions are at large horizontal displacements (offsets) as well as benzene/benzene interactions. The interactions at large horizontal displacements are stabilized by the addition of simultaneous interactions in supramolecular structures in crystals. The stacking p-phenol/p-phenol tends to be orientated in a parallel and antiparallel fashion, while stacking toluene/toluene is almost all in an antiparallel orientation. It is in accordance with calculated interaction energies. Namely, the strongest interaction energies for parallel and antiparallel phenol/phenol dimers are −5.12 and −4.40 kcal/mol, at offsets of 1.5 and 3.0 Å, respectively, while for parallel and antiparallel toluene/toluene dimers, energies are −3.98 and −5.39 kcal/mol, at offsets of 3.0 Å. These interactions are stronger than benzene/benzene stacking (−2.85 kcal/mol), as a consequence of the presence of the substituents. Similar to benzene/benzene stacking, interactions for phenol/phenol and toluene/toluene stacking at large offsets (4.0 Å) can be strong, stronger than −2.0 kcal/mol.