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

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.