2,2′-Bipyridine

2,2′-Bipyridine
Skeletal formula of 2,2′-bipyridine
Ball-and-stick model of the 2,2′-bipyridine molecule
Space-filling model of the 2,2′-bipyridine molecule
Names
Preferred IUPAC name
2,2′-Bipyridine
Other names
Bipyridyl
Dipyridyl
Bipy
Bpy
Dipy
Identifiers
CAS Number
  • 366-18-7 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
 113089
ChEBI
  • CHEBI:30351 checkY
ChEMBL
  • ChEMBL39879 checkY
ChemSpider
  • 13867714 checkY
ECHA InfoCard 100.006.069 Edit this at Wikidata
EC Number
  • 206-674-4 923-456-0
Gmelin Reference
 3720 936807
PubChem CID
  • 1474
RTECS number
  • DW1750000
UNII
  • 551W113ZEP checkY
CompTox Dashboard (EPA)
  • DTXSID9040635 Edit this at Wikidata
InChI
  • InChI=1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H checkY
    Key: ROFVEXUMMXZLPA-UHFFFAOYSA-N checkY
  • InChI=1/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H
    Key: ROFVEXUMMXZLPA-UHFFFAOYAP
  • n1ccccc1-c2ccccn2
Properties
Chemical formula
 C10H8N2
Molar mass 156.188 g·mol−1
Appearance Colorless solid
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
Occupational safety and health (OHS/OSH):
Main hazards
 toxic
GHS labelling:
GHS06: ToxicGHS07: Exclamation mark
Danger
H301, H302, H311, H312, H319, H412
P264, P270, P273, P280, P301+P310, P301+P312, P302+P352, P305+P351+P338, P312, P321, P322, P330, P337+P313, P361, P363, P405, P501
Lethal dose or concentration (LD, LC):
15-78 mg/kg (oral, rat); 20-140 mg/kg (oral, mouse)
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).
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Infobox references
Chemical compound

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 and platinum complexes of bipy exhibit intense luminescence, which may have practical applications.

Preparation, structure, and general properties

2,2'-Bipyridine was first prepared by decarboxylation of divalent metal derivatives of pyridine-2-carboxylate:[1]

M(O2CC5H4N)2 → (C5H4N)2 + 2 CO2 + ...

It is prepared by the dehydrogenation of pyridine using Raney nickel:[2]

2 C5H5N → (C5H4N)2 + H2

Substituted 2,2'-bipyridines

Unsymmetrically substituted 2,2'-bipyridines can be prepared by cross coupling reaction of 2-pyridyl and substituted pyridyl reagents.[3]

Structure

Although 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.[4] Monoprotonated bipyridine adopts a cis conformation.[5]

Reactions

A large number of complexes of 2,2'-bipyridine have been described. It binds metals as a chelating ligand, forming a 5-membered chelate ring.

See also

References

  1. ^ Constable; Housecroft (2019). "The Early Years of 2,2'-Bipyridine—A Ligand in its Own Lifetime". Molecules. 24 (21): 3951. doi:10.3390/molecules24213951. PMC 6864536. PMID 31683694.
  2. ^ Sasse, W. H. F. (1966). "2,2′-Bipyridine". Organic Syntheses. 46: 5; Collected Volumes, vol. 5, p. 102.
  3. ^ Liu, Tiandong; Fraser, Cassandra L. (2012). "Discussion Addendum for: Synthesis of 4-, 5-, and 6-Methyl-2,2'-bipyridine by a Negishi Cross-Coupling Strategy: 5-Methyl-2,2'-bipyridine". Organic Syntheses. 89: 76. doi:10.15227/orgsyn.089.0076.
  4. ^ Merritt, L. L.; Schroeder, E. (1956). "The Crystal Structure of 2,2′-Bipyridine". Acta Crystallographica. 9 (10): 801–804. doi:10.1107/S0365110X56002175.
  5. ^ Göller, A.; Grummt, U.-W. (2000). "Torsional barriers in biphenyl, 2,2′-bipyridine and 2-phenylpyridine". Chemical Physics Letters. 321 (5–6): 399–405. Bibcode:2000CPL...321..399G. doi:10.1016/S0009-2614(00)00352-3.