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4-Pyridylnicotinamide

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4-Pyridylnicotinamide
4-pyridylnicotinamide sketch
Names
Preferred IUPAC name N-(Pyridin-4-yl)pyridine-3-carboxamide
Other names 4-PNA; N-4-Pyridinyl-3-pyridinecarboxamide,; N-(Pyridin-4-yl)nicotinamide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C11H9N3O/c15-11(9-2-1-5-13-8-9)14-10-3-6-12-7-4-10/h1-8H,(H,12,14,15)Key: HVLLFBPOFNSPRN-UHFFFAOYSA-N
SMILES
  • O=C(Nc1ccncc1)c2cccnc2
Properties
Chemical formula C11H9N3O
Molar mass 199.213 g·mol
Density 1.287 g/cm
Boiling point 286.08 °C (546.94 °F; 559.23 K)
Structure
Dipole moment 0 D
Related compounds
Related compounds 4,4'-bipyridine
Pyridine
Nicotinamide
4-Aminopyridine
3-Pyridylnicotinamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. 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. It is synthesized through the reaction of nicotinoyl chloride and 4-aminopyridine.

References

  1. ^ Gardner, T. S.; Wenis, E.; Lee, J. (1954). "The Synthesis of Compounds for the Chemotherapy of Tuberculosis. Iv. The Amide Function". The Journal of Organic Chemistry. 19 (5): 753. doi:10.1021/jo01370a009.
  2. Kraft, P. E.; Laduca, R. L. (2012). "catena-Poly[[tetra-μ-benzoato-κO:O′-dicopper(II)]-μ-[N-(pyridin-4-yl)nicotinamide]-κN:N′-[dibenzoato-κO-copper(II)]-μ-[N-(pyridin-4-yl)nicotinamide]-κN:N′]". Acta Crystallographica Section E. 68 (8): m1049–m1050. doi:10.1107/S1600536812030437. PMC 3414118. PMID 22904725.
  3. Krishna Kumar, D. (2009). "Exploring the effect of chain length of bridging ligands in coordination complexes and polymers derived from mixed ligand systems of pyridylnicotinamides and dicarboxylates". Inorganica Chimica Acta. 362 (6): 1767–2013. doi:10.1016/j.ica.2008.08.033.
  4. Kumar, D. K.; Das, A.; Dastidar, P. (2006). "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. doi:10.1021/cg0600344.
  5. Kumar, D. K.; Das, A.; Dastidar, P. (2006). "Exploring hydrogen-bond capable backbone and ligating topologies: Co(II) coordination polymers derived from mixed ligand systems". Journal of Molecular Structure. 796 (1–3): 139–145. Bibcode:2006JMoSt.796..139K. doi:10.1016/j.molstruc.2006.02.033.


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