| Revision as of 16:07, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475471591 of page 1,2-Bis(dimethylarsino)benzene for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 14:49, 7 September 2024 edit JWBE (talk | contribs)Extended confirmed users10,111 edits removed Category:Benzene derivatives; added Category:Phenylene compounds using HotCat |
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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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| verifiedrevid = 442344616 |
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| verifiedrevid = 477203033 |
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| ImageFile = Diars.png |
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| ImageFile = Diars.png |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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| ImageName1 = Ball and stick model of 1,2-bis(dimethylarsino)benzene |
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| ImageName1 = Ball and stick model of 1,2-bis(dimethylarsino)benzene |
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| PIN = (1,2-Phenylene)bis(dimethylarsane) |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = DAS, Diars |
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| Abbreviations = DAS, Diars |
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| CASNo = <!-- blanked - oldvalue: 13246-32-7 --> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 83261 |
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| CASNo = 13246-32-7 |
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| PubChem_Ref = {{Pubchemcite|correct|pubchem}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChemSpiderID = 75125 |
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| UNII = K3C0GW5M57 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| EINECS = 236-227-9 |
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| PubChem = 83261 |
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| ChemSpiderID = 75125 |
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| MeSHName = 2-Phenylene-bis-dimethylarsine |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI = 30628 |
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| EINECS = 236-227-9 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| MeSHName = 2-Phenylene-bis-dimethylarsine |
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| Beilstein = 2937031 |
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| Gmelin = 3780 |
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| ChEBI = 30628 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES = C(C)c1ccccc1(C)C |
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| Beilstein = 2937031 |
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| SMILES1 = C(C)C1=CC=CC=C1(C)C |
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| Gmelin = 3780 |
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| StdInChI = 1S/C10H16As2/c1-11(2)9-7-5-6-8-10(9)12(3)4/h5-8H,1-4H3 |
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| SMILES = C(C)c1ccccc1(C)C |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| SMILES1 = C(C)C1=CC=CC=C1(C)C |
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| InChI = 1/C10H16As2/c1-11(2)9-7-5-6-8-10(9)12(3)4/h5-8H,1-4H3 |
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| StdInChI = 1S/C10H16As2/c1-11(2)9-7-5-6-8-10(9)12(3)4/h5-8H,1-4H3 |
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| StdInChIKey = HUBWRAMPQVYBRS-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = 1/C10H16As2/c1-11(2)9-7-5-6-8-10(9)12(3)4/h5-8H,1-4H3 |
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| InChIKey = HUBWRAMPQVYBRS-UHFFFAOYAM |
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| StdInChIKey = HUBWRAMPQVYBRS-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey = HUBWRAMPQVYBRS-UHFFFAOYAM |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = {{Chem|C|10|As|2|H|16}} |
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| Formula = {{Chem|C|10|As|2|H|16}} |
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| MolarMass = 286.0772 g mol<sup>-1</sup> |
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| MolarMass = 286.0772 g mol{{sup|−1}} |
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| Appearance = Colourless liquid |
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| ExactMass = 285.968393346 g mol<sup>-1</sup> |
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| Density = 1.3992 g cm{{sup|−3}} |
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| Appearance = Colourless liquid |
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| BoilingPtC = 97 to 101 |
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| Density = 1.3992 g cm<sup>-3</sup> |
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| BoilingPt_notes = at 150 Pa |
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| BoilingPtCL = 97 |
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| BoilingPtCH = 101 |
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| Boiling_notes = at 150 Pa |
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| Section3 = {{Chembox Hazards |
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| MainHazards = Toxic |
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| MainHazards = Toxic |
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'''1,2-Bis(dimethylarsino)benzene''' ('''diars''') is the ] with the ] C{{sub|6}}H{{sub|4}}(As(CH{{sub|3}}){{sub|2}}){{sub|2}}. The molecule consists of two di]arsino groups attached to adjacent carbon centers of a ] ring. It is a ] ] in ]. This colourless oil is commonly abbreviated "diars."<ref>Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. {{ISBN|0-12-352651-5}}.</ref> |
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==Coordination chemistry== |
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Related, but non-chelating organoarsenic ligands include ] and ]. Work on diars preceded the development of the chelating diphosphine ligands such as ], which are now prevalent in ]. |
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Diars is a bidentate ligand used in coordination chemistry. It was first described in 1939,<ref>], J.; Mann, F. G. "The Synthesis of Ditertiary Arsines. Meso- and Racemic Forms of Bis-4-Covalent-Arsenic Compounds" Journal of the Chemical Society, 1939, 610–615. {{doi|10.1039/JR9390000610}}</ref> but was popularized by ] for its ability to stabilize metal complexes with unusual oxidation states and coordination numbers, e.g. TiCl{{sub|4}}(diars){{sub|2}}. High coordination numbers arise because diars is fairly compact and the As-M bonds are long, which relieves crowding at the metal center. In terms of stabilizing unusual oxidation states, diars stabilizes Ni(III), as in Cl. |
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Of historical interest is the supposedly diamagnetic (ClO{{sub|4}}){{sub|2}}, obtained by heating nickel perchlorate with diars. Octahedral ''d''{{sup|8}} complexes characteristically have triplet ground states, so the diamagnetism of this complex was puzzling. Later by ], the complex was shown to be pentacoordinate with the formula (ClO{{sub|4}}){{sub|2}}, where triars is the tridentate ligand {{sub|2}}As(CH{{sub|3}}), arising from the elimination of ].<ref>B. Bosnich, R. S. Nyholm, P. J. Pauling, M. L. Tobe "A nickel(II)-catalyzed synthesis of a triarsine from a diarsine" J. Am. Chem. Soc. 1968, volume 90, pp 4741–4742. {{doi|10.1021/ja01019a049}}</ref><ref>Anthony Nicholl Rail; ''Some new reactions of a ditertiary arsine ligand''; Ph.D. Thesis; University College London; 1973</ref> |
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==Preparation and handling== |
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Diars is prepared by the reaction of ] and sodium dimethylarsenide:<ref>Feltham, R. D.; Silverthorn, W. "''o''-Phenylenebis(dimethylarsine)" Inorganic Syntheses 1967, Vol. X, pp. 159–164. {{doi|10.1002/9780470132418.ch24}}</ref> |
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:C{{sub|6}}H{{sub|4}}Cl{{sub|2}} + 2 NaAs(CH{{sub|3}}){{sub|2}} → C{{sub|6}}H{{sub|4}}(As(CH{{sub|3}}){{sub|2}}){{sub|2}} + 2 NaCl |
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It is a colorless liquid. Oxygen converts diars to the dioxide, C{{sub|6}}H{{sub|4}}(As(CH{{sub|3}}){{sub|2}}O){{sub|2}}. |
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== References == |
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{{Reflist}} |
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{{DEFAULTSORT:Bis(dimethylarsino)benzene, 1, 2-}} |
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] |
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] |
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] |