| Revision as of 15:42, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 457310474 of page 2,2'-Bipyridine for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 03:28, 9 December 2024 edit WikiCleanerBot (talk | contribs)Bots925,164 editsm v2.05b - Bot T20 CW#61 - Fix errors for CW project (Reference before punctuation)Tag: WPCleaner |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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|Watchedfields = changed |
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| verifiedrevid = 413094920 |
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|verifiedrevid = 477198878 |
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| Name = 2,2'-Bipyridine |
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|Name = 2,2′-Bipyridine |
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| ImageFile = Bipy-2D-skeletal.png |
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|ImageFile = Centro-bipyHoroz.png |
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<!-- | ImageSize = 188px --> |
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|ImageSize = 150 |
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| ImageName = 2,2'-bipyridine |
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|ImageAlt = Skeletal formula of 2,2′-bipyridine |
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| IUPACName = 2,2'-Bipyridine |
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|ImageFile1 = 2,2′-bipyridine-from-xtal-view-2-3D-bs-17.png |
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| OtherNames = Bipyridyl<br />Dipyridyl<br />Bipy<br />Bpy<br />Dipy |
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|ImageSize1 = 180 |
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| Section1 = {{Chembox Identifiers |
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|ImageAlt1 = Ball-and-stick model of the 2,2′-bipyridine molecule |
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| InChI = 1/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H |
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|ImageFile2 = 2,2′-bipyridine-from-xtal-view-2-3D-sf.png |
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| InChIKey = ROFVEXUMMXZLPA-UHFFFAOYAP |
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|ImageSize2 = 180 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|ImageAlt2 = Space-filling model of the 2,2′-bipyridine molecule |
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| ChEMBL = 39879 |
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|ImageFile3 = 2,2'-bipyridine sample.jpg |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|ImageSize3 = 150 |
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| StdInChI = 1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H |
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|PIN = 2,2′-Bipyridine |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|OtherNames = Bipyridyl<br />Dipyridyl<br />Bipy<br />Bpy<br />Dipy |
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| StdInChIKey = ROFVEXUMMXZLPA-UHFFFAOYSA-N |
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|Section1={{Chembox Identifiers |
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| CASNo = 366-18-7 |
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|InChI = 1/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H |
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| UNII = 551W113ZEP |
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|InChIKey = ROFVEXUMMXZLPA-UHFFFAOYAP |
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| SMILES = c1ccnc(c1)c2ccccn2 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 30351 |
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|ChEMBL = 39879 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChemSpiderID = 13867714 |
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|StdInChI = 1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H |
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| RTECS = DW1750000 |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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|StdInChIKey = ROFVEXUMMXZLPA-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|C=10|H=8|N=2 |
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|CASNo = 366-18-7 |
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| Density = |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| MeltingPt = 70-73 °C |
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|UNII = 551W113ZEP |
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| BoilingPt = 273 °C |
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|SMILES = n1ccccc1-c2ccccn2 |
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}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Section3 = {{Chembox Structure |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| CrystalStruct = |
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|ChEBI = 30351 |
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| Dipole = 0 ] |
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|ChemSpiderID = 13867714 |
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}} |
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|RTECS = DW1750000 |
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| Section7 = {{Chembox Hazards |
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|PubChem = 1474 |
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| ExternalMSDS = |
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|EC_number = 206-674-4 923-456-0 |
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| MainHazards = toxic |
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|Beilstein = 113089 |
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| FlashPt = |
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|Gmelin = 3720 936807 |
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| RPhrases = 25 |
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| SPhrases = 36/37-45 |
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}} |
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| Section8 = {{Chembox Related |
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| OtherCpds = ]<br/>]<br />]<br />]<br />] |
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}} |
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|Section2={{Chembox Properties |
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|Formula={{chem2|(C5H4N)2}} |
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|Appearance = Colorless solid |
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|MeltingPtC = 70 to 73 |
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|BoilingPtC = 273 |
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}} |
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|Section3={{Chembox Structure |
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|Dipole = 0 ] |
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}} |
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|Section7={{Chembox Hazards |
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|MainHazards = toxic |
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|LD50 = 15-78 mg/kg (oral, rat); 20-140 mg/kg (oral, mouse) |
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|GHSPictograms = {{GHS06}}{{GHS07}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|301|302|311|312|319|412}} |
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|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}} |
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}} |
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|Section8={{Chembox Related |
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| OtherCompounds = ]<br/>]<br />]<br />]<br />]<br />] |
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}} |
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'''2,2′-Bipyridine''' ('''bipy''' or '''bpy''', pronounced {{IPAc-en|ˈ|b|ɪ|p|iː}}) is an ] with the formula {{Chem2|(C5H4N)|auto=yes}}. This colorless solid is an important ] of the ] family. It is a ] ] ], forming complexes with many ]s. ] and ] complexes of bipy exhibit intense ].{{citation needed|date=December 2024}} |
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==Preparation, structure, and general properties== |
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2,2'-Bipyridine was first prepared by decarboxylation of divalent metal derivatives of ]:<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> |
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{{chem2|2C5H4NCOO- -> (C5H4N)2 + 2CO2 + 2e-}} |
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It is prepared by the ] of ] using ]:<ref>{{OrgSynth | author = Sasse, W. H. F. | title = 2,2′-Bipyridine | year = 1966 | volume = 46 | pages = 5 | collvol = 5 | collvolpages = 102 | prep = cv5p0102 }}</ref> |
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{{chem2|2C5H5N -> (C5H4N)2 + H2}} |
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===Substituted 2,2'-bipyridines=== |
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Unsymmetrically substituted 2,2'-bipyridines can be prepared by ] 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> |
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==Structure== |
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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> |
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] |
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==Reactions== |
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2,2'-bipyridine produces ]. It binds metals as a ] ], forming a 5-membered chelate ring. |
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==See also== |
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* ] |
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* ] |
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* ] |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Bipyridine, 2,2'-}} |
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] |
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] |
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] |