The 2-Aminopyridinium-carboxylate Supramolecular Heterosynthon: A Robust Motif for Generation of Multiple-Component Crystals

• DOI: 10.1021/cg049622c
• Publication Date: 2005-05-04T04:24:22Z
• Authors: Joanna A. Bis; Michael J. Zaworotko
• Keywords: Moiety; Carboxylate; Synthon; Crystal Engineering

An analysis of the Cambridge Structural Database reveals that 77% compounds contain both 2-aminopyridine and carboxylic acid moieties generate 2-aminopyridine-carboxylic supramolecular heterosynthons rather than or homosynthons. In absence other competing functionalities, occurrence increases to 97%. This observation is supported by determination single-crystal structures 10 new a moiety: 2-aminopyridinium 4-aminobenzoate, 1; isophthalate, 2; bis(2-aminopyridinium) terephthalate, 3; 2-amino-5-methylpyridinium benzoate, 4; bis(2-amino-5-methylpyridinium) 5-tertbutylisophthalate, 5; 6; 2,6-naphthalenedicarboxylate, 7; adipate adipic acid, 8; 2,5-thiophenedicarboxylate 2,5-thiophenedicarboxylic 9; indomethacin 2-amino-5-methylpyridinium, 10. All are ionic, with proton transfer occurring aromatic nitrogen moiety. Analysis synthons their effect upon crystal packing presented in context engineering host−guest chemistry.