2,2′-Bipyridine on:
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2,2′-Bipyridine (bipy or bpy, pronounced ) is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with the formula C10H8N2. This colorless solid is an important isomer of the bipyridine Bipyridines also known as bipyridyls, dipyridyls, and dipyridines, are a family of chemical compounds with the formula (C5H4N)2, consisting of two pyridyl (C5H4N) rings. Pyridine is an aromatic nitrogen-containing heterocycle. Bipyridines are of si ...
family. It is a bidentate chelating
Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These ligands are ...
ligand
In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elec ...
, forming complexes with many transition metal
In chemistry, a transition metal (or transition element) is a chemical element in the d-block of the periodic table (groups 3 to 12), though the elements of group 12 (and less often group 3) are sometimes excluded. They are the elements that ca ...
s. Ruthenium
Ruthenium is a chemical element with the symbol Ru and atomic number 44. It is a rare transition metal belonging to the platinum group of the periodic table. Like the other metals of the platinum group, ruthenium is inert to most other chemical ...
and platinum
Platinum is a chemical element with the symbol Pt and atomic number 78. It is a dense, malleable, ductile, highly unreactive, precious, silverish-white transition metal. Its name originates from Spanish , a diminutive of "silver".
Pla ...
complexes of bipy exhibit intense luminescence
Luminescence is spontaneous emission of light by a substance not resulting from heat; or "cold light".
It is thus a form of cold-body radiation. It can be caused by chemical reactions, electrical energy, subatomic motions or stress on a crys ...
, 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: :M(O2CC5H4N)2 → (C5H4N)2 + 2CO2 + ... It is prepared by thedehydrogenation
In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At ...
of pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a ...
using Raney nickel:
:2C5H5N → (C5H4N)2 + H2
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
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
* 2,2'-Biquinoline * 1,10-PhenanthrolineReferences
{{DEFAULTSORT:Bipyridine, 2,2'- Chelating agents Bipyridines