Covalent-Assisted Supramolecular Synthesis: Masking of Amides in Co-Crystal Synthesis using Benzophenone Derivatives

Abstract

Control over hydrogen bonding patterns and the dimensionality of supramolecular structures is possible through covalent-assisted supramolecular synthesis. Consistent and predictable “masking” of the amide functionality has been achieved through the covalent modification of isoniazid with benzophenone and benzophenone derivatives while co-crystallizing with salicylic acid. A series of co-crystals using benzophenones as masking agents were prepared using one-pot synthetic methods. No short intermolecular contacts were present between the amide nitrogen atoms in isoniazid and neighboring isoniazid or salicylic acid atoms.