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4,4'-Bipyridine

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4,4′-Bipyridine
4,4′-bipyridine
4,4′-Bipyridine molecule
Names
Preferred IUPAC name
4,4′-Bipyridine
Identifiers
3D model (JSmol)
113176
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.216 Edit this at Wikidata
EC Number
  • 209-036-3
3759
UNII
  • InChI=1S/C10H8N2/c1-5-11-6-2-9(1)10-3-7-12-8-4-10/h1-8H ☒N
    Key: MWVTWFVJZLCBMC-UHFFFAOYSA-N ☒N
  • c1cnccc1-c2ccncc2
Properties
C10H8N2
Molar mass 156.188 g·mol−1
Melting point 114 °C (237 °F; 387 K)
Boiling point 305 °C (581 °F; 578 K)
Structure
D
Related compounds
Related compounds
2,2′-Bipyridine
Pyridine
4-Pyridylnicotinamide
Terpyridine
Biphenyl
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

4,4′-Bipyridine (abbreviated to 4,4′-bipy or 4,4′-bpy) is a bipyridine which is mainly used as a precursor to N,N′-dimethyl-4,4′-bipyridinium [(C5H4NCH3)2]2+, known as paraquat. This species is electroactive, and its toxicity arises from the ability of this dication to interrupt biological electron transfer. Because of its structure, 4,4′-bipyridine can bridge between metal centres to give coordination polymers.[1] 4,4′-Bipyridine can also mediate electronic effects between two paramagnetic metal centers.[2]

History

4,4′-Bipyridine was first obtained in 1868 by the Scottish chemist Thomas Anderson (1819–1874) via heating pyridine with sodium metal.[3] However, Anderson's empirical formula for 4,4′-bipyridine was incorrect.[4] The correct empirical formula, and the correct molecular structure, for 4,4′-bipyridine was provided in 1882 by the Austrian chemist Hugo Weidel and his student M. Russo.[5]

Uses

4,4'-Bipyridine is an intermediate in the production of paraquat, a widely-used herbicide. In this process, pyridine is oxidized to 4,4'-bipyridine in a coupling reaction, followed by dimethylation to form paraquat.[6]

References

  1. ^ Biradha, K.; Sarkar, M.; Rajput, L. (2006). "Crystal engineering of coordination polymers using 4,4′-bipyridine as a bond between transition metal atoms". Chemical Communications (40): 4169–79. doi:10.1039/B606184B. PMID 17031423.
  2. ^ Zeng, M.-H.; Zhang, W.-X.; Sun, X.-Z.; Chen, X.-M. (2005). "Spin Canting and Metamagnetism in a 3D Homometallic Molecular Material Constructed by Interpenetration of Two Kinds of Cobalt(II)-Coordination-Polymer Sheets". Angewandte Chemie International Edition. 44 (20): 3079. doi:10.1002/anie.200462463. PMID 15770632.
  3. ^ See:
  4. ^ Anderson gave the empirical formula for 4,4′-bipyridine as C10H10N2. See:
    • (Anderson, 1868), p. 209.
    • (Fehling, 1890), p. 974 (γ-Dipyridyl).
  5. ^ Weidel, H.; Russo, M. (1882). "Studien über das Pyridin" [Studies of pyridine]. Monatshefte für Chemie (in German). 3: 850–885. The empirical formula for 4,4′-bipyridine (γ-Dipyridyl) appears on p. 856 ; the molecular structure of 4,4′-bipyridine (γ-Dipyridyl) appears on p. 867.
  6. ^ "Paraquat and Diquat". IPCS INCHEM.