4-Pyridylnicotinamide Explained

4-Pyridylnicotinamide (4-PNA), also known as N-(pyridin-4-yl)nicotinamide, is a kinked dipodal dipyridine which was originally developed for use in chemotherapy.^[1] As in its isomer 3-pyridylnicotinamide, the nitrogen atoms on its pyridine rings can donate their electron lone pairs to metal cations, allowing it to bridge metal centers and act as a bidentate ligand in coordination polymers.^{[2] [3] [4] [5]} It is synthesized through the reaction of nicotinoyl chloride and 4-aminopyridine.

Notes and References

1. Gardner . T. S. . Wenis . E. . Lee . J. . 10.1021/jo01370a009 . The Synthesis of Compounds for the Chemotherapy of Tuberculosis. Iv. The Amide Function . The Journal of Organic Chemistry . 19 . 5 . 753 . 1954 .
2. Kraft . P. E. . Laduca . R. L. . 10.1107/S1600536812030437 . catena-Poly[<nowiki/>[tetra-μ-benzoato-κ⁸''O'':''O''′-dicopper(II)]-μ-[''N''-(pyridin-4-yl)nicotinamide]-κ²N:N′-[dibenzoato-κ²''O''-copper(II)]-μ-[''N''-(pyridin-4-yl)nicotinamide]-κ²N:N′] . Acta Crystallographica Section E . 68 . 8 . m1049–m1050 . 2012 . 22904725. 3414118.
3. Krishna Kumar . D. . Exploring the effect of chain length of bridging ligands in coordination complexes and polymers derived from mixed ligand systems of pyridylnicotinamides and dicarboxylates . 10.1016/j.ica.2008.08.033 . Inorganica Chimica Acta . 362 . 6 . 1767–2013 . 2009 .
4. Kumar . D. K. . Das . A. . Dastidar . P. . 10.1021/cg0600344 . One-Dimensional Chains, Two-Dimensional Corrugated Sheets Having a Cross-Linked Helix in Metal−Organic Frameworks: Exploring Hydrogen-Bond Capable Backbones and Ligating Topologies in Mixed Ligand Systems . Crystal Growth & Design . 6 . 8 . 1903 . 2006 .
5. Kumar . D. K. . Das . A. . Dastidar . P. . Exploring hydrogen-bond capable backbone and ligating topologies: Co(II) coordination polymers derived from mixed ligand systems . 10.1016/j.molstruc.2006.02.033 . Journal of Molecular Structure . 796 . 1–3 . 139–145 . 2006 . 2006JMoSt.796..139K .