2,2'-bipyridine

2,2'-Bipyridine
Names


Preferred IUPAC name 2,2'-Bipyridine
Other names Bipyridyl Dipyridyl Bipy Bpy Dipy
Identifiers
CAS Number	366-18-7
3D model (Jmol)	Interactive image
ChEBI	CHEBI:30351
ChEMBL	ChEMBL39879^Y
ChemSpider	13867714^Y
ECHA InfoCard	100.006.069
RTECS number	DW1750000
UNII	551W113ZEP
InChI InChI=1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H^Y Key: ROFVEXUMMXZLPA-UHFFFAOYSA-N^Y InChI=1/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H Key: ROFVEXUMMXZLPA-UHFFFAOYAP
SMILES n1ccccc1-c2ccccn2
Properties
Chemical formula	C₁₀H₈N₂
Molar mass	156.19 g·mol⁻¹
Melting point	70 to 73 °C (158 to 163 °F; 343 to 346 K)
Boiling point	273 °C (523 °F; 546 K)
Structure
Dipole moment	0 D
Hazards
Main hazards	toxic
R-phrases	25
S-phrases	36/37-45
Related compounds
Related compounds	4,4′-Bipyridine Pyridine Phenanthroline 3-Pyridylnicotinamide Terpyridine Biphenyl
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

2,2′-Bipyridine (bipy or bpy, pronounced /ˈbɪpiː/) is an organic compound with the formula (C₁₀H₈N₂). This colorless solid is an important isomer of the bipyridine family. It is a bidentate chelating ligand, forming complexes with many transition metals. Ruthenium complex and platinum complexes of bipy exhibit intense luminescence, which may have practical applications.

It is prepared by the dehydrogenation of pyridine using Raney nickel:

Although uncoordinated bipyridine is often drawn with its nitrogen atoms in cis conformation, the lowest energy conformation both in solid state and in solution is in fact coplanar, with nitrogen atoms in trans position. Protonated bipyridine adopts a cis conformation. Upon binding to metal ions the related N,N-heterocyclic ligand phenanthroline does not incur an enthalpic and entropic penalty, and thus its complexes tend to be more stable.

Reflecting the popularity of this ligand design, many substituted variants of bipy have been described.

Bipyridine complexes absorb intensely in the visible part of the spectrum. The electronic transitions are attributed to metal-to-ligand charge transfer (MLCT). In the "tris(bipy) complexes" three bipyridine molecules coordinate to a metal ion, written as [M(bipy)₃]ⁿ⁺ (M = metal ion; Cr, Fe, Co, Ru, Rh and so on; bipy = 2,2′-bipyridine). These complexes have six-coordinated, octahedral structures and two enantiomers as follows:

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