4,4'-Bipyridine

4,4′-Bipyridine
Names
	IUPAC name 4,4′-Bipyridine
Identifiers
CAS Number	553-26-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	113176
ChEBI	CHEBI:30985 ;
ChEMBL	ChEMBL1374568;
ChemSpider	10636 ;
ECHA InfoCard	100.008.216
EC Number	209-036-3;
Gmelin Reference	3759
PubChem CID	11107;
UNII	X4O2OD61CB;
CompTox Dashboard (EPA)	DTXSID2027200 ;
	InChI InChI=1S/C10H8N2/c1-5-11-6-2-9(1)10-3-7-12-8-4-10/h1-8H Key: MWVTWFVJZLCBMC-UHFFFAOYSA-N ;
	SMILES c1cnccc1-c2ccncc2;
Properties
Chemical formula	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
Dipole moment	0 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).
	verify (what is ?)
	Infobox references

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]

gollark: ^

gollark: Why not have some sort of sensibly escapable JSON message format for webhooks?

gollark: Stupidly.

gollark: You should just display `[USER INPUT]` because discord is stuoidly textual.

gollark: What was that 1433 KST then?

References

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.
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.
See:
- Anderson, Thomas (1868). "On the products of the destructive distillation of animal substances. Part V." Transactions of the Royal Society of Edinburgh. 25: 205–216. Anderson called 4,4′-bipyridine "Dipyridine".
- German translation: Anderson, Th. (1870). "Ueber die Producte der trockenen Destillation thierischer Materien. Fünfter Theil" [On the products of the dry distillation of animal materials. Fifth part.]. Annalen der Chemie und Pharmacie (in German). 154: 270–286.
- See also: Fehling, Hermann Christian von, ed. (1890). Neues Handwörterbuch der Chemie [New Concise Dictionary of Chemistry] (in German). vol. 5. Braunschweig, Germany: Friedrich Vieweg und Sohn. p. 974. See γ-Dipyridyl.
Anderson gave the empirical formula for 4,4′-bipyridine as C₁₀H₁₀N₂. See:
- (Anderson, 1868), p. 209.
- (Fehling, 1890), p. 974 (γ-Dipyridyl).
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.
"Paraquat and Diquat". IPCS INCHEM.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[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:
Anderson, Thomas (1868). "On the products of the destructive distillation of animal substances. Part V." Transactions of the Royal Society of Edinburgh. 25: 205–216. Anderson called 4,4′-bipyridine "Dipyridine".

German translation: Anderson, Th. (1870). "Ueber die Producte der trockenen Destillation thierischer Materien. Fünfter Theil" [On the products of the dry distillation of animal materials. Fifth part.]. Annalen der Chemie und Pharmacie (in German). 154: 270–286.

See also: Fehling, Hermann Christian von, ed. (1890). Neues Handwörterbuch der Chemie [New Concise Dictionary of Chemistry] (in German). vol. 5. Braunschweig, Germany: Friedrich Vieweg und Sohn. p. 974. See γ-Dipyridyl.

[4] Anderson, Thomas (1868). "On the products of the destructive distillation of animal substances. Part V." Transactions of the Royal Society of Edinburgh. 25: 205–216. Anderson called 4,4′-bipyridine "Dipyridine".

[5] German translation: Anderson, Th. (1870). "Ueber die Producte der trockenen Destillation thierischer Materien. Fünfter Theil" [On the products of the dry distillation of animal materials. Fifth part.]. Annalen der Chemie und Pharmacie (in German). 154: 270–286.

[6] See also: Fehling, Hermann Christian von, ed. (1890). Neues Handwörterbuch der Chemie [New Concise Dictionary of Chemistry] (in German). vol. 5. Braunschweig, Germany: Friedrich Vieweg und Sohn. p. 974. See γ-Dipyridyl.

[4] Anderson gave the empirical formula for 4,4′-bipyridine as C₁₀H₁₀N₂. See:
(Anderson, 1868), p. 209.

(Fehling, 1890), p. 974 (γ-Dipyridyl).

[8] (Anderson, 1868), p. 209.

[9] (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.