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.[3] Monoprotonated bipyridine adopts a cis conformation.[4]
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.
^Constable; Housecroft (2019). "The Early Years of 2,2'-Bipyridine—A Ligand in its Own Lifetime". Molecules. 24 (21): 3951. doi:10.3390/molecules24213951. PMC6864536. PMID 31683694.
^Sasse, W. H. F. (1966). "2,2′-Bipyridine". Organic Syntheses. 46: 5.; Collective Volume, vol. 5, p. 102
^Merritt, L. L.; Schroeder, E. (1956). "The Crystal Structure of 2,2′-Bipyridine". Acta Crystallographica. 9 (10): 801–804. doi:10.1107/S0365110X56002175.
^Göller, A.; Grummt, U.-W. (2000). "Torsional barriers in biphenyl, 2,2′-bipyridine and 2-phenylpyridine". Chemical Physics Letters. 321 (5–6): 399–405. Bibcode:2000CPL...321..399G. doi:10.1016/S0009-2614(00)00352-3.
January 29, 2023
bipyridine, bipy, pronounced, organic, compound, with, formula, c10h8n2, this, colorless, solid, important, isomer, bipyridine, family, bidentate, chelating, ligand, forming, complexes, with, many, transition, metals, ruthenium, platinum, complexes, bipy, exhi. 2 2 Bipyridine bipy or bpy pronounced 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 chelating ligand forming complexes with many transition metals Ruthenium and platinum complexes of bipy exhibit intense luminescence which may have practical applications 2 2 Bipyridine NamesPreferred IUPAC name 2 2 BipyridineOther names BipyridylDipyridylBipyBpyDipyIdentifiersCAS Number 366 18 7 Y3D model JSmol Interactive imageBeilstein Reference 113089ChEBI CHEBI 30351 YChEMBL ChEMBL39879 YChemSpider 13867714 YECHA InfoCard 100 006 069EC Number 206 674 4 923 456 0Gmelin Reference 3720 936807PubChem CID 1474RTECS number DW1750000UNII 551W113ZEP YCompTox Dashboard EPA DTXSID9040635InChI InChI 1S C10H8N2 c1 3 7 11 9 5 1 10 6 2 4 8 12 10 h1 8H YKey ROFVEXUMMXZLPA UHFFFAOYSA N YInChI 1 C10H8N2 c1 3 7 11 9 5 1 10 6 2 4 8 12 10 h1 8HKey ROFVEXUMMXZLPA UHFFFAOYAPSMILES n1ccccc1 c2ccccn2PropertiesChemical formula C 10H 8N 2Molar mass 156 188 g mol 1Appearance Colorless solidMelting point 70 to 73 C 158 to 163 F 343 to 346 K Boiling point 273 C 523 F 546 K StructureDipole moment 0 DHazardsOccupational safety and health OHS OSH Main hazards toxicGHS labelling PictogramsSignal word DangerHazard statements H301 H302 H311 H312 H319 H412Precautionary statements P264 P270 P273 P280 P301 P310 P301 P312 P302 P352 P305 P351 P338 P312 P321 P322 P330 P337 P313 P361 P363 P405 P501Lethal dose or concentration LD LC LD50 median dose 15 78 mg kg oral rat 20 140 mg kg oral mouse Related compoundsRelated compounds 4 4 BipyridinePyridinePhenanthroline3 PyridylnicotinamideTerpyridineBiphenylExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Preparation structure and general properties 2 Reactions 3 See also 4 ReferencesPreparation structure and general properties Edit2 2 Bipyridine was first prepared by decarboxylation of divalent metal derivatives of pyridine 2 carboxylate 1 M O2CC5H4N 2 C5H4N 2 2 CO2 It is prepared by the dehydrogenation of pyridine using Raney nickel 2 2 C5H5N C5H4N 2 H2Although 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 3 Monoprotonated bipyridine adopts a cis conformation 4 Reactions EditA 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 Edit2 2 Biquinoline 1 10 PhenanthrolineReferences Edit Constable Housecroft 2019 The Early Years of 2 2 Bipyridine A Ligand in its Own Lifetime Molecules 24 21 3951 doi 10 3390 molecules24213951 PMC 6864536 PMID 31683694 Sasse W H F 1966 2 2 Bipyridine Organic Syntheses 46 5 Collective Volume vol 5 p 102 Merritt L L Schroeder E 1956 The Crystal Structure of 2 2 Bipyridine Acta Crystallographica 9 10 801 804 doi 10 1107 S0365110X56002175 Goller A Grummt U W 2000 Torsional barriers in biphenyl 2 2 bipyridine and 2 phenylpyridine Chemical Physics Letters 321 5 6 399 405 Bibcode 2000CPL 321 399G doi 10 1016 S0009 2614 00 00352 3 Retrieved from https en wikipedia org w index php title 2 2 Bipyridine amp oldid 1094851932, wikipedia, wiki, book, books, library,
