Synthesis and Structural Characterization of Organophosphorus Ylide-1-(3-nitrophenyl)-2-(triphenyl phosphoranylidene)ethanone
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摘要
The title compound Ph3P=C(H)C(O)PhNO2(L) has been prepared by the addition of triphenylphosphine in acetone as solvent to 2-bromo-1-(3-nitrophenyl)ethanone followed by the addition of alkaline solution of sodium hydroxide. The yellow crystals of the title ylide were grown in methanol/chloroform solution by drop method without stirring at room temperature. The solid state structure of ylide has been established by X-ray crystallography analysis. In the molecule of the title compound, the geometry around the P atom is nearly tetrahedral and the O atom is in synperiplanar orientation to the P atom. The nitrophenyl ring is twisted with respect to the plane of the carbonyl group through an angle of 36.6(1)°. The crystal(C26H20NO3P, Mr = 425.40) belongs to the monoclinic system, space group P21/n with a = 10.889(3), b = 14.467(3), c = 13.872(4) , β = 103.08(3)°, V = 2128.6(10) 3, Z = 4, T = 100(2) K, R = 0.059 and w R = 0.163 for 3984 observed reflections with Ⅰ >2σ(Ⅰ).
The title compound Ph3P=C(H)C(O)PhNO2(L) has been prepared by the addition of triphenylphosphine in acetone as solvent to 2-bromo-1-(3-nitrophenyl)ethanone followed by the addition of alkaline solution of sodium hydroxide. The yellow crystals of the title ylide were grown in methanol/chloroform solution by drop method without stirring at room temperature. The solid state structure of ylide has been established by X-ray crystallography analysis. In the molecule of the title compound, the geometry around the P atom is nearly tetrahedral and the O atom is in synperiplanar orientation to the P atom. The nitrophenyl ring is twisted with respect to the plane of the carbonyl group through an angle of 36.6(1)°. The crystal(C26H20NO3P, Mr = 425.40) belongs to the monoclinic system, space group P21/n with a = 10.889(3), b = 14.467(3), c = 13.872(4) , β = 103.08(3)°, V = 2128.6(10) 3, Z = 4, T = 100(2) K, R = 0.059 and w R = 0.163 for 3984 observed reflections with Ⅰ >2σ(Ⅰ).
The title compound Ph3P=C(H)C(O)PhNO2(L) has been prepared by the addition of triphenylphosphine in acetone as solvent to 2-bromo-1-(3-nitrophenyl)ethanone followed by the addition of alkaline solution of sodium hydroxide. The yellow crystals of the title ylide were grown in methanol/chloroform solution by drop method without stirring at room temperature. The solid state structure of ylide has been established by X-ray crystallography analysis. In the molecule of the title compound, the geometry around the P atom is nearly tetrahedral and the O atom is in synperiplanar orientation to the P atom. The nitrophenyl ring is twisted with respect to the plane of the carbonyl group through an angle of 36.6(1)°. The crystal(C26H20NO3P, Mr = 425.40) belongs to the monoclinic system, space group P21/n with a = 10.889(3), b = 14.467(3), c = 13.872(4) , β = 103.08(3)°, V = 2128.6(10) 3, Z = 4, T = 100(2) K, R = 0.059 and w R = 0.163 for 3984 observed reflections with Ⅰ >2σ(Ⅰ).
引文
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(16)Coldham,I.;Hufton,R.Intramolecular dipolar cycloaddition reactions of azomethine ylides.Chem.Rev.2005,105,2765-2810.
(17)Burton,D.J.;Yang,Z.Y.;Qiu,W.Fluorinated ylides and related compounds.Chem.Rev.1996,96,1641-1716.
(18)Gilheany,D.G.Ylides,phosphoniumno d orbitals but Walsh diagrams and mybe banana bonds:chemical bonding in phosphines,phosphine oxides,and phosphonium ylides.Chem.Rev.1994,94,1339-1374.
(19)Thanikaivelan,P.;Subraminanian,V.;Raghava,R.J.;Nair,B.U.Application of quantum chemical descriptor in quantitative structure activity and structure property relationship.Chem.Phys.Lett.2000,323,59-70.
(20)Allen,F.H.;Kennard,O.;Watson,D.G.;Brammer,L.;Orpen,A.G.;Taylor,R.Tables of bond lengths determined by X-ray and neutron diffraction.Part 1.Bond lengths in organic compounds.J.Chem.Soc.Perkin Trans.II 1987,S1–S19.
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(22)Chattaraj,P.K.;Poddar,A.Molecular reactivity in the ground and excited electronic states through density-dependent local and global reactivity parameters.J.Phys.Chem.A 1999,103,8691-8699.
(2)Johnson,A.W.Ylides and Imines of Phosphorus,John Wiley&Sons,New York,USA 1993.
(3)Vedejs,E.;West,F.G.Ylides by the desilylation of alpha-silylonium salts.Chem.Rev.1986,86,941-955.
(4)Dadrass,A.R.;Ebrahimnezhad,S.;Pourmirza,M.;Poursattar Marjani,A.Synthesis and characterization of labile ylide of1-(p-tolyl)-2-(tri-p-tolylphosphoranylidene)ethanone and its related complexes with mercury(II)halides.Current Chem.Lett.2014,3,103-108.
(5)(a)Becke,A.D.Density‐functional thermochemistry.III.The role of exact exchange.J.Chem.Phys.1993,98,5648-5652.(b)Lee,C.;Yang,W.;Parr,R.G.Development of the colle-salvetti correlation-energy formula into a functional of the electron density.Phys.Rev.B 1988,37,785-789.
(6)Stevens,W.J.;Basch,H.;Krauss,M.Compact effective potentials and efficient shared-exponent basis sets for the first-and second-row atoms,J.Chem.Phys.1984,81,6026-6033.
(7)Frisch,M.J.;Trucks,G.W.;Schlegel,H.B.;Scuseria,G.E.;Robb,M.A.;Cheeseman,J.R.;Montgomery,J.A.;Vreven,J.T.;Kudin,K.N.;Burant,J.C.;Millam,J.M.;Iyengar,S.S.;Tomasi,J.;Barone,V.;Mennucci,B.;Cossi,M.;Scalmani,G.;Rega,N.;Petersson,G.A.;Nakatsuji,H.;Hada,M.;Ehara,M.;Toyota,K.;Fukuta,R.;Hasegawa,J.;Ishida,M.;Nakajima,T.;Honda,Y.;Kitao,O.;Nakai,H.;Klene,M.;Au,X.;Knox,J.E.;Hratchian,H.P.;Cross,J.B.;Adamo,C.;Jaramillo,J.;Gomperts,R.;Stratmann,R.E.;Yazyev,O.;Austin,A.J.;Cammi,R.;Pomelli,C.;Ochterski,J.W.;Ayala,P.Y.;Morokuma,K.;Voth,G.A.;Salvador,P.;Dannenberg,J.J.;Zakrzewski,V.G.;Dapprich,S.;Daniels,A.D.;Strain,M.C.;Farkas,O.;Malick,D.K.;Rabuck,A.D.;Raghavachari,K.;Foresman,J.B.;Ortiz,J.V.;Cui,Q.;Baboul,A.G.;Clifford,S.;Cioslowski,J.;Stefanov,B.B.;Auu,G.;Auashenko,A.;Piskorz,P.;Komaromi,I.;Martin,R.L.;Fox,D.J.;Keith,T.;AI-Laham,M.A.;Peng,C.Y.;Nanayakkara,A.;Challacombe,M.;Gill,P.M.W.;Johnson,B.;Chen,W.;Wong,M.W.;Gonzalez,C.;Pople,J.A.Gaussian 03,Revision A.1.;Gaussian,Inc.:Pittsburgh,PA 2003.
(8)Crys Alis CCD and Crys Alis RED in Xcalibur PX software.Oxford Diffraction Ltd,Yarnton,Oxfordshire,England 2009.
(9)Sheldrick,G.M.A short history of SHELX.Acta Crystallogr.2008,A64,112-122.
(10)Brandenburg,K.Diamond.Crystal Impact Gb R.Bonn,Germany 2012.
(11)Coyne,E.J.;Gilheany,D.G.Comprehensive Organic Functional Group Transformation 1995,Vol 3,Chap 3.13,Pattenden,G.Vol Ed,Katritzky,A.R.;Meth-Cohn,O.;Rees,C.W.Eds in Chief,Pergamon Press,Elsevier,Oxford,UK.
(12)Kolodiazhnyi,O.I.Phosphorus Ylides.Wiley-VCH,Weinheim,Germany 1999.
(13)Clark,J.S.Nitrogen,Oxygen and Sulfur Ylide Chemistry.Oxford University Press,Oxford,UK 2002.
(14)Kolodiazhnyi,O.I.C-element-substituted phosphorus ylids.Tetrahedron 1996,52,1855-1929.
(15)Padwa,A.;Hornbuckle,S.F.Ylide formation from the reaction of carbenes and carbenoids with heteroatom lone pairs.Chem.Rev.1991,91,263-309.
(16)Coldham,I.;Hufton,R.Intramolecular dipolar cycloaddition reactions of azomethine ylides.Chem.Rev.2005,105,2765-2810.
(17)Burton,D.J.;Yang,Z.Y.;Qiu,W.Fluorinated ylides and related compounds.Chem.Rev.1996,96,1641-1716.
(18)Gilheany,D.G.Ylides,phosphoniumno d orbitals but Walsh diagrams and mybe banana bonds:chemical bonding in phosphines,phosphine oxides,and phosphonium ylides.Chem.Rev.1994,94,1339-1374.
(19)Thanikaivelan,P.;Subraminanian,V.;Raghava,R.J.;Nair,B.U.Application of quantum chemical descriptor in quantitative structure activity and structure property relationship.Chem.Phys.Lett.2000,323,59-70.
(20)Allen,F.H.;Kennard,O.;Watson,D.G.;Brammer,L.;Orpen,A.G.;Taylor,R.Tables of bond lengths determined by X-ray and neutron diffraction.Part 1.Bond lengths in organic compounds.J.Chem.Soc.Perkin Trans.II 1987,S1–S19.
(21)Pearson,R.G.Absolute electronegativity and hardness:application to inorganic chemistry.Inorg.Chem.1988,27,734-740.
(22)Chattaraj,P.K.;Poddar,A.Molecular reactivity in the ground and excited electronic states through density-dependent local and global reactivity parameters.J.Phys.Chem.A 1999,103,8691-8699.