2,2′-Bipyridine
<templatestyles src="Chembox/styles.css"/>
Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox headerbarTemplate:Chembox HazardsTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Yesno| Template:Longitem | Template:Unbulleted list |
| Template:Longitem | 113089 |
| ChEBI | Template:Unbulleted list |
| ChemSpider | Template:Unbulleted list |
| DrugBank | Template:Unbulleted list |
| EC Number | Template:Unbulleted list |
| Template:Longitem | 3720 936807 |
| KEGG | Template:Unbulleted list |
| Template:Longitem | Template:Unbulleted list |
| RTECS number | Template:Unbulleted list |
| Script error: No such module "collapsible list". | |
| Script error: No such module "collapsible list". | |
| Template:Longitem | Template:Chem2 |
| Molar mass | 156.18 |
| Appearance | Colorless solid |
| Melting point | Template:Chembox CalcTemperatures |
| Boiling point | Template:Chembox CalcTemperatures |
| Template:Longitem | 0 D |
| Template:Longitem | 4,4′-Bipyridine Pyridine Phenanthroline 3-Pyridylnicotinamide Terpyridine Biphenyl |
Template:Chembox Footer/tracking container onlyScript error: No such module "TemplatePar".Template:Short description
2,2′-Bipyridine (bipy or bpy, pronounced Template:IPAc-en)Script error: No such module "Unsubst". is an organic compound with the formula Template:Chem2. 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.[1]
Preparation, structure, and general properties
2,2'-Bipyridine was first prepared by decarboxylation of divalent metal derivatives of pyridine-2-carboxylate:[2]
It is prepared by the dehydrogenation of pyridine using Raney nickel:[3]
Substituted 2,2'-bipyridines
Unsymmetrically substituted 2,2'-bipyridines can be prepared by cross coupling reaction of 2-pyridyl and substituted pyridyl reagents.[4]
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.[5] Monoprotonated bipyridine adopts a cis conformation.[6]
File:Cis-monoprotonated-2,2′-bipyridine-from-xtal-3D-bs-17.png
Reactions
2,2'-bipyridine produces multiple coordination complexes. It binds metals as a ligand for chelation, forming a 5-membered chelate ring.
See also
References
<templatestyles src="Reflist/styles.css" />
Script error: No such module "Check for unknown parameters".