Synthesis of multicomponent crystals composed of 4-amino-1-methylpyridinium p-toluenesulfonate and phenol derivatives

Preparation of crystals containing three chemical species was investigated using two ionic components of 4-amino-1-methylpyridinium p-toluenesulfonate (AP-TS) and one more molecular component from phenol derivatives. Oxygen atoms at the sulfonate group of TS act as hydrogen-bonding acceptors while hydrogen atoms at the hydroxy group of phenol derivatives as well as at the amino group of AP act as hydrogen-bonding donors, and hydrogen bonding among these species helps to form three-component cocrystals. Among ten phenol derivatives investigated, 4,4'-biphenol and (+/-)-1,1'-bi-2-naphthol cocrystallized with AP-TS. From these crystal structure studies, we found a common structural feature based on the hydrogen-bonding patterns.