Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2,2′-Bipyridine: Difference between pages

|Watchedfields = changed

|verifiedrevid = 477198878

|Name = 2,2′-Bipyridine

|ImageFile = Centro-bipyHoroz.png

|ImageSize = 150

|ImageAlt = Skeletal formula of 2,2′-bipyridine

|ImageFile1 = 2,2′-bipyridine-from-xtal-view-2-3D-bs-17.png

|ImageSize1 = 180

|ImageAlt1 = Ball-and-stick model of the 2,2′-bipyridine molecule

|ImageFile2 = 2,2′-bipyridine-from-xtal-view-2-3D-sf.png

|ImageSize2 = 180

|ImageAlt2 = Space-filling model of the 2,2′-bipyridine molecule

|ImageFile3 = 2,2'-bipyridine sample.jpg

|ImageSize3 = 150

|PIN = 2,2′-Bipyridine

|OtherNames = Bipyridyl<br />Dipyridyl<br />Bipy<br />Bpy<br />Dipy

|Section1={{Chembox Identifiers

|InChI = 1/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H

|InChIKey = ROFVEXUMMXZLPA-UHFFFAOYAP

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 39879

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = ROFVEXUMMXZLPA-UHFFFAOYSA-N

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo = 366-18-7

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = 551W113ZEP

|SMILES = n1ccccc1-c2ccccn2

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEBI = 30351

|ChemSpiderID = 13867714

|RTECS = DW1750000

|PubChem = 1474

|EC_number = 206-674-4 923-456-0

|Beilstein = 113089

|Gmelin = 3720 936807

|Section2={{Chembox Properties

|C=10 | H=8 | N=2

|Appearance = Colorless solid

|MeltingPtC = 70 to 73

|BoilingPtC = 273

}}

|Section3={{Chembox Structure

|Dipole = 0 [[Debye|D]]

}}

|Section7={{Chembox Hazards

|MainHazards = toxic

|LD50 = 15-78 mg/kg (oral, rat); 20-140 mg/kg (oral, mouse)

|GHSPictograms = {{GHS06}}{{GHS07}}

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|301|302|311|312|319|412}}

|PPhrases = {{P-phrases|264|270|273|280|301+310|301+312|302+352|305+351+338|312|321|322|330|337+313|361|363|405|501}}

}}

|Section8={{Chembox Related

| OtherCompounds = [[4,4'-Bipyridine|4,4′-Bipyridine]]<br/>[[Pyridine]]<br />[[Phenanthroline]]<br />[[3-Pyridylnicotinamide]]<br />[[Terpyridine]]<br />[[Biphenyl]]

}}

}}

'''2,2′-Bipyridine''' ('''bipy''' or '''bpy''', pronounced {{IPAc-en|ˈ|b|ɪ|p|iː}}) is an [[organic compound]] with the formula C₁₀H₈N₂. This colorless solid is an important [[isomer]] of the [[bipyridine]] family. It is a [[bidentate]] [[chelation|chelating]] [[ligand]], forming complexes with many [[transition metal]]s. [[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-carboxylic acid|pyridine-2-carboxylate]]:<ref name=Constacraft>{{cite journal |doi=10.3390/molecules24213951|doi-access=free|title=The Early Years of 2,2'-Bipyridine—A Ligand in its Own Lifetime|year=2019|last1=Constable|last2=Housecroft|journal=Molecules|volume=24|issue=21|page=3951|pmid=31683694|pmc=6864536}}</ref>

:M(O₂CC₅H₄N)₂ → (C₅H₄N)₂ + 2{{nbsp}}CO₂ + ...

It is prepared by the [[dehydrogenation]] of [[pyridine]] using [[Raney nickel]]:<ref>{{OrgSynth | author = Sasse, W. H. F. | title = 2,2′-Bipyridine | year = 1966 | volume = 46 | pages = 5 | collvol = 5 | collvolpages = 102 | prep = cv5p0102 }}</ref>

:2{{nbsp}}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.<ref>{{cite journal |doi=10.15227/orgsyn.089.0076 |title=Discussion Addendum for: Synthesis of 4-, 5-, and 6-Methyl-2,2'-bipyridine by a Negishi Cross-Coupling Strategy: 5-Methyl-2,2'-bipyridine |journal=Organic Syntheses |date=2012 |volume=89 |page=76|first1=Tiandong|last1=Liu|first2=Cassandra L.|last2=Fraser }}</ref>

==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.<ref>{{cite journal |author1=Merritt, L. L. |author2=Schroeder, E. | title = The Crystal Structure of 2,2′-Bipyridine | journal = Acta Crystallographica | year = 1956 | volume = 9 | issue = 10 | pages = 801–804 | doi = 10.1107/S0365110X56002175| doi-access = free }}</ref> Monoprotonated bipyridine adopts a ''cis'' conformation.<ref>{{cite journal |author1=Göller, A. |author2=Grummt, U.-W. | title = Torsional barriers in biphenyl, 2,2′-bipyridine and 2-phenylpyridine | journal = Chemical Physics Letters | year = 2000 | volume = 321 | issue = 5–6 | pages = 399–405 | doi = 10.1016/S0009-2614(00)00352-3 |bibcode=2000CPL...321..399G}}</ref>

[[File:Cis-monoprotonated-2,2′-bipyridine-from-xtal-3D-bs-17.png|200px]]

==Reactions==

A large number of [[Transition metal complexes of 2,2'-bipyridine|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-Phenanthroline]]

* [[Dimethyl-2,2'-bipyridine]]

==References==

{{reflist}}

{{DEFAULTSORT:Bipyridine, 2,2'-}}

[[Category:Chelating agents]]

[[Category:Bipyridines]]

[[Category:2-Pyridyl compounds]]