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2,2′-Bipyridine

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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
3D model (JSmol)
Beilstein Reference 113089
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.069 Edit this at Wikidata
EC Number
  • 206-674-4 923-456-0
Gmelin Reference 3720 936807
PubChem CID
RTECS number
  • DW1750000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8HKey: ROFVEXUMMXZLPA-UHFFFAOYSA-N
  • InChI=1/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8HKey: ROFVEXUMMXZLPA-UHFFFAOYAP
SMILES
  • n1ccccc1-c2ccccn2
Properties
Chemical formula (C5H4N)2
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:
Pictograms GHS06: ToxicGHS07: Exclamation mark
Signal word Danger
Hazard statements H301, H302, H311, H312, H319, H412
Precautionary statements 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):
LD50 (median dose) 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

2,2′-Bipyridine (bipy or bpy, pronounced /ˈbɪpiː/) is an organic compound with the formula (C5H4N). 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.

Preparation, structure, and general properties

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

2C5H4NCOO → (C5H4N)2 + 2CO2 + 2e

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

2C5H5N → (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.

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. Monoprotonated bipyridine adopts a cis conformation.

Reactions

2,2'-bipyridine produces multiple coordination complexes. 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.
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