4,4'-Bipyridine

4,4'-Bipyridine

Names
IUPAC name 4,4'-Bipyridine
Identifiers
CAS Number	553-26-4
ChEBI	CHEBI:30985
ChemSpider	10636
Jmol interactive 3D	Image
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 C1(C2=CC=NC=C2)=CC=NC=C1
Properties
Chemical formula	C10H8N2
Molar mass	156.19 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).
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Infobox references

4,4'-Bipyridine (4,4'-bipy) 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'-bpy can also mediate electronic effects between two paramagnetic metal centers.^[2]

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.