Supriya Ghosh (Editor)

2,2' Bipyridine

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Formula  C10H8N2
Boiling point  273 °C
2,2'-Bipyridine File2239Bipyridine structurepng Wikimedia Commons
Related compounds  4,4′-Bipyridine Pyridine Phenanthroline 3-Pyridylnicotinamide Terpyridine Biphenyl

2,2′-Bipyridine (bipy or bpy, pronounced /ˈbɪp/) 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.

Contents

2,2'-Bipyridine Bipyridine Wikipedia

Preparation and general properties

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

2C5H5N → (C5H4N)2 + H2 2,2'-Bipyridine 2239Bipyridine CAS 366187 103098

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.

Illustrative complexes

2,2'-Bipyridine Bipyridine Wikipedia
  • Mo(CO)4(bipy), derived from Mo(CO)6.
  • RuCl2(bipy)2, a useful precursor to mixed ligand complexes.
  • [Ru(bipy)3]Cl2, a well known luminophore.
  • [Fe(bipy)3]2+ is used for the colorimetric analysis of iron ions.
  • Tris-bipy complexes

    2,2'-Bipyridine httpsuploadwikimediaorgwikipediacommonsthu

    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:

    2,2'-Bipyridine 22Bipyridyl ReagentPlus 99 C10H8N2 SigmaAldrich

    These and other homoleptic tris-2,2′-bipy complexes of many transition metals are electroactive. Often, both the metal centred and ligand centred electrochemical reactions are reversible one-electron reactions that can be observed by cyclic voltammetry. Under strongly reducing conditions, most tris(bipy) complexes can be reduced to neutral derivatives containing bipy ligands. Examples include M(bipy)3, where M = Al, Cr, Si.

    2,2'-Bipyridine 2239bipyridine Wikiwand
    2,2'-Bipyridine Tris22bipyridinedichlororutheniumII hexahydrate technical

    References

    2,2'-Bipyridine Wikipedia


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