3-Pyridylnicotinamide Explained

The organic compound 3-pyridylnicotinamide (3-pna), also known as N-(pyridin-3-yl)nicotinamide, is a kinked dipodal dipyridine that is synthesized through the reaction of nicotinoyl chloride and 3-aminopyridine.^[1] The nitrogen atoms on its pyridine rings, like those of its isomer 4-pyridylnicotinamide, 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] [6]} It can be used to synthesize polymers that have potentially useful gas adsorption properties.

Notes and References

1. Zheng . X. . Salgia . S. R. . Thompson . W. B. . Dillingham . E. O. . Bond . S. E. . Feng . Z. . Prasad . K. R. . Gollamudi . R. . 10.1021/jm00001a023 . Design and Synthesis of Piperidine-3-carboxamides as Human Platelet Aggregation Inhibitors . Journal of Medicinal Chemistry . 38 . 1 . 180–188 . 1995 . 7837229.
2. Uemura . K. . Kitagawa . S. . Fukui . K. I. . Saito . K. . A Contrivance for a Dynamic Porous Framework: Cooperative Guest Adsorption Based on Square Grids Connected by Amide−Amide Hydrogen Bonds . 10.1021/ja039914m . Journal of the American Chemical Society . 126 . 12 . 3817–3828 . 2004 . 15038736.
3. Uemura . K. . Kitagawa . S. . Kondo . M. . Fukui . K. I. . Kitaura . R. . Chang . H. C. . Mizutani . T. . 10.1002/1521-3765(20020816)8:16<3586::AID-CHEM3586>3.0.CO;2-K . Novel Flexible Frameworks of Porous Cobalt(II) Coordination Polymers That Show Selective Guest Adsorption Based on the Switching of Hydrogen-Bond Pairs of Amide Groups . Chemistry: A European Journal . 8 . 16 . 3586–4100 . 2002 . 12203285 .
4. Kumar . D. K. . Das . A. . Dastidar . P. . 10.1039/B701782K . Supramolecular structural diversities in the metal?organic frameworks derived from pyridylamide ligands: Studying the effects of ligating topologies, hydrogen bonding backbone of the ligands and counter anions . CrystEngComm . 9 . 7 . 548 . 2007 .
5. Banerjee . S. . Adarsh . N. N. . Dastidar . P. . 10.1002/ejic.201000359 . Selective Separation of the Sulfate Anion by in Situ Crystallization of CdII Coordination Compounds Derived from Bis(pyridyl) Ligands Equipped with a Urea/Amide Hydrogen-Bonding Backbone . European Journal of Inorganic Chemistry . 2010 . 24 . 3770 . 2010 .
6. Kumar . D. K. . Das . A. . Dastidar . P. . 10.1039/B705851A . Conformation dependent network structures in the coordination polymers derived from pyridylisonicotinamides, carboxylates and Co(ii): Entrapment of (H2O)14 water cluster of an unprecedented topology . CrystEngComm. Royal Society of Chemistry. 9 . 10 . 895 . 2007 .