2,2′-Bipyridine

changed 477198878 2,2′-Bipyridine Centro-bipyHoroz.png skin-invert-image 150 Skeletal formula of 2,2′-bipyridine 2,2′-bipyridine-from-xtal-view-2-3D-bs-17.png bg-transparent 180 Ball-and-stick model of the 2,2′-bipyridine molecule 2,2′-bipyridine-from-xtal-view-2-3D-sf.png bg-transparent 180 Space-filling model of the 2,2′-bipyridine molecule 2,2'-bipyridine sample.jpg 150 2,2′-Bipyridine BipyridylDipyridylBipyBpyDipy 1/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H ROFVEXUMMXZLPA-UHFFFAOYAP correct EBI 39879 correct chemspider 1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H correct chemspider ROFVEXUMMXZLPA-UHFFFAOYSA-N correct CAS 366-18-7 correct FDA 551W113ZEP n1ccccc1-c2ccccn2 correct chemspider correct EBI 30351 13867714 DW1750000 1474 206-674-4 923-456-0 113089 3720 936807 (C5H4N)2 10 8 2 Colorless solid 70 to 73 273 0 D toxic 15-78 mg/kg (oral, rat); 20-140 mg/kg (oral, mouse) 06 07 Danger 301 302 311 312 319 412 264 270 273 280 301+310 301+312 302+352 305+351+338 312 321 322 330 337+313 361 363 405 501 4,4′-BipyridinePyridinePhenanthroline3-PyridylnicotinamideTerpyridineBiphenyl 2,2′-Bipyridine (bipy or bpy, pronounced ˈ b ɪ p iː)April 2025 is an organic compound with the formula (C5H4N)2 yes. 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.Broomhead J. A. Young C. G. Tris(2,2″-Bipyridine)Ruthenium(II) Dichloride Hexahydrate 1990 Inorganic Syntheses 28 338–340 10.1002/9780470132593.ch86 978-0-470-13259-3 Preparation, structure, and general properties 2,2'-Bipyridine was first prepared by decarboxylation of divalent metal derivatives of pyridine-2-carboxylate:10.3390/molecules24213951 free The Early Years of 2,2'-Bipyridine—A Ligand in its Own Lifetime 2019 Constable Housecroft Molecules 24 21 3951 31683694 6864536 2C5H4NCOO- -> (C5H4N)2 + 2CO2 + 2e- It is prepared by the dehydrogenation of pyridine using Raney nickel: Sasse, W. H. F. 2,2′-Bipyridine 1966 46 5 10.15227/orgsyn.046.0005 2C5H5N -> (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.10.15227/orgsyn.089.0076 free Discussion Addendum for: Synthesis of 4-, 5-, and 6-Methyl-2,2'-bipyridine by a Negishi Cross-Coupling Strategy: 5-Methyl-2,2'-bipyridine Organic Syntheses 2012 89 76 Tiandong Liu Cassandra L. Fraser 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.Merritt, L. L. Schroeder, E. The Crystal Structure of 2,2′-Bipyridine Acta Crystallographica 1956 9 10 801–804 10.1107/S0365110X56002175 free Monoprotonated bipyridine adopts a cis conformation.Göller, A. Grummt, U.-W. Torsional barriers in biphenyl, 2,2′-bipyridine and 2-phenylpyridine Chemical Physics Letters 2000 321 5–6 399–405 10.1016/S0009-2614(00)00352-3 2000CPL...321..399G 200px Reactions 2,2'-bipyridine produces multiple coordination complexes. It binds metals as a ligand for chelation, forming a 5-membered chelate ring. See also 2,2'-Biquinoline 1,10-Phenanthroline Dimethyl-2,2'-bipyridine References Category:Chelating agents Category:Bipyridines Category:2-Pyridyl compounds Category:Symmetrical biaryls