2-Acetaminopyridine: A Highly Effective Cocrystallizing Agent

To take advantage of the 2-aminopyridine moiety as a structural and geometric supramolecular complement to carboxylic acids while avoiding transforming two neutral molecular building blocks into an ion-pair during noncovalent assembly, 2-acetaminopyridine (2-AApy) has been explored as a potential cocrystallizing agent. The crystal structures of eight cocrystals are presented. Each contain the same expected hydrogen-bonded motifs, and there has been no proton transfer from either of the eight carboxylic acids to the pyridine moiety. This demonstrates that 2-AApy is very capable of affecting the construction of binary cocrystals in a predictable and rationale manner.