Quantitative Analyses of Molecular Surface Electrostatic Potentials in Relation to Hydrogen Bonding and Co-Crystallization

The important role that electrostatic potentials computed on molecular surfaces can have in designing new materials via co-crystallization is discussed and illustrated. The locally most positive and most negative values of the surface electrostatic potential identify and rank sites for hydrogen bonding (complementing Etter’s rules), halogen bonding, and other types of noncovalent interactions. It is shown that the primary interactions are often better viewed as involving small regions rather than specific atoms. Recent applications of cocrystallization as a means of reducing the hazard associated with energetic materials are briefly examined.