Infrared, Sn-119, C-13 and H-1 NMR, Sn-119 and C-13 CP/MAS NMR and Mossbauer spectral study of some tributylstannyl citrates and propane-1,2,3-tricarboxylates
Six tributylstannyl citrates and three tributylstannyl propane-1,2,3-tricarboxylates of the formula (RC)-C-1(CH2COOR2)(COOR3)(CH2COOR4) (R-1 = OH or H, R-2, R-3, R-4 = H, Bu3Sn, C6H11NH3, (C6H11)(2)NH2 or (CH2)(5)NH2) have been synthesised, and their solution and solid-state structures studied by in...
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Published in | Collection of Czechoslovak chemical communications Vol. 64; no. 6; pp. 1028 - 1048 |
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Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
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PRAGUE 6
Inst Organic Chem And Biochem
01.06.1999
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Abstract | Six tributylstannyl citrates and three tributylstannyl propane-1,2,3-tricarboxylates of the formula (RC)-C-1(CH2COOR2)(COOR3)(CH2COOR4) (R-1 = OH or H, R-2, R-3, R-4 = H, Bu3Sn, C6H11NH3, (C6H11)(2)NH2 or (CH2)(5)NH2) have been synthesised, and their solution and solid-state structures studied by infrared, H-1,C-13 and Sn-119 NMR, C-13 and Sn-119 CP/MAS NMR and Sn-119 Mossbauer spectroscopies. In non-coordinating solvents, the compounds exist as isolated molecules or ionic-pairs with their tin atoms in pseudotetrahedral environments. In coordinating solvents, the tin atoms in the compounds are five-coordinate owing to the participation of the solvent in bonding; and their trans-trigonal bipyramidal coordination spheres consist of the ipso-carbon atoms of the butyl substituents in equatorial plane, and the solvent molecule and the oxygen atom of the monodentate carboxyl group in axial positions. A part of tributylstannyl groups together with some bidentate bridging carboxylate groups form polymeric chains in the solid state of citrates and propane-1,2,3-tricarboxylates. Also dioxastanna-rings with the participation alpha-hydroxycarboxylate fragments and one of the tributylstannyl groups occur probably in some citrates in the solid state. The spectroscopic assignment for the citrate has been confirmed by crystal structure analysis. Key words: Stannanes; Organotin compounds; Citrates; Propane-1,2,3-tricarboxylates; IR spectroscopy; NMR spectroscopy,H-1, C-13 and Sn-119; CP/MAS NMR spectroscopy,C-13 and Sn-119; Mossbauer spectroscopy; Crystal structure. |
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AbstractList | Six tributylstannyl citrates and three tributylstannyl propane-1,2,3-tricarboxylates of the formula (RC)-C-1(CH2COOR2)(COOR3)(CH2COOR4) (R-1 = OH or H, R-2, R-3, R-4 = H, Bu3Sn, C6H11NH3, (C6H11)(2)NH2 or (CH2)(5)NH2) have been synthesised, and their solution and solid-state structures studied by infrared, H-1,C-13 and Sn-119 NMR, C-13 and Sn-119 CP/MAS NMR and Sn-119 Mossbauer spectroscopies. In non-coordinating solvents, the compounds exist as isolated molecules or ionic-pairs with their tin atoms in pseudotetrahedral environments. In coordinating solvents, the tin atoms in the compounds are five-coordinate owing to the participation of the solvent in bonding; and their trans-trigonal bipyramidal coordination spheres consist of the ipso-carbon atoms of the butyl substituents in equatorial plane, and the solvent molecule and the oxygen atom of the monodentate carboxyl group in axial positions. A part of tributylstannyl groups together with some bidentate bridging carboxylate groups form polymeric chains in the solid state of citrates and propane-1,2,3-tricarboxylates. Also dioxastanna-rings with the participation alpha-hydroxycarboxylate fragments and one of the tributylstannyl groups occur probably in some citrates in the solid state. The spectroscopic assignment for the citrate has been confirmed by crystal structure analysis. Key words: Stannanes; Organotin compounds; Citrates; Propane-1,2,3-tricarboxylates; IR spectroscopy; NMR spectroscopy,H-1, C-13 and Sn-119; CP/MAS NMR spectroscopy,C-13 and Sn-119; Mossbauer spectroscopy; Crystal structure. |
Author | Vanko, G Brus, J Holecek, J Ng, SW Lycka, A Fun, HK Nagy, L Raj, SSS Micak, D |
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Keywords | organotin compounds CRYSTAL-STRUCTURE COMPLEXES stannanes COORDINATION citrates IR spectroscopy H-1 C-13 and Sn-119 CP/MAS NMR spectroscopy Mossbauer spectroscopy crystal structure propane-1,2,3-tricarboxylates NMR spectroscopy CARBOXYLIC-ACIDS |
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References | Ng, SW (WOS:000074825000022) 1998; 54 TIEKINK, ERT (WOS:A1991EW37800001) 1991; 5 HARTLEY, DW (WOS:A1991GK05900036) 1991 SHELDRICK GM (WOS:000081630000012.22) 1997 DEACON, GB (WOS:A1980KX69200002) 1980; 33 LEVY GC (WOS:000081630000012.13) 1980 NG, SW (WOS:A1988N177000007) 1988; 345 BAKER, EN (WOS:A1983QW82300008) 1983; 78 BLUNDEN SJ (WOS:000081630000012.4) 1985 HANSEN PE (WOS:000081630000012.7) 1992; 2 KORECZ, L (WOS:A1982NG69300039) 1982; 58 NG, SW (WOS:A1992JB76000002) 1992; 430 Deacon, PR (WOS:A1997YD75000009) 1997 MERWIN, LH (WOS:A1992HR29400015) 1992; 30 SHELDRICK, GM (WOS:A1990DJ92700008) 1990; 46 ZUCKERMAN JJ (WOS:000081630000012.25) 1970; 9 NG, SW (WOS:A1990DQ80900003) 1990; 390 BATES RG (WOS:000081630000012.3) 1941; 71 JOB, R (WOS:A1982PJ85700032) 1982; 21 HOLECEK, J (WOS:A1986D898700007) 1986; 118 Holecek, J (WOS:A1997WM58200012) 1997; 62 TIEKINK ERT (WOS:000081630000012.24) 1994; 1 NADVORNIK, M (WOS:A1984TQ66500007) 1984; 275 NG SW (WOS:000081630000012.17) 1999; 55 BANCROFT, GM (WOS:A1976BP19600017) 1976 |
References_xml | – volume: 2 start-page: 153 year: 1992 ident: WOS:000081630000012.7 publication-title: CHEM ACID DERIVAT SB contributor: fullname: HANSEN PE – year: 1985 ident: WOS:000081630000012.4 publication-title: IND USE TIN COMPOUND contributor: fullname: BLUNDEN SJ – volume: 33 start-page: 227 year: 1980 ident: WOS:A1980KX69200002 article-title: RELATIONSHIPS BETWEEN THE CARBON-OXYGEN STRETCHING FREQUENCIES OF CARBOXYLATO COMPLEXES AND THE TYPE OF CARBOXYLATE COORDINATION publication-title: COORDINATION CHEMISTRY REVIEWS contributor: fullname: DEACON, GB – volume: 118 start-page: L15 year: 1986 ident: WOS:A1986D898700007 article-title: DEPENDENCE OF [1J(SN-119C-13)] ON THE C-SN-C ANGLE IN NORMAL-BUTYLTIN(IV) COMPOUNDS publication-title: INORGANICA CHIMICA ACTA contributor: fullname: HOLECEK, J – volume: 345 start-page: 59 year: 1988 ident: WOS:A1988N177000007 article-title: THE REPEAT DISTANCE IN CARBOXYLATE-BRIDGED TRIORGANOTIN(IV) CARBOXYLATE POLYMERS publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: NG, SW – year: 1980 ident: WOS:000081630000012.13 publication-title: CARBON 13 NUCL MAGNE contributor: fullname: LEVY GC – volume: 9 start-page: 21 year: 1970 ident: WOS:000081630000012.25 publication-title: ADVAN ORGANOMETAL CH contributor: fullname: ZUCKERMAN JJ – year: 1997 ident: WOS:000081630000012.22 publication-title: SHELXL97 PROGRAM REF contributor: fullname: SHELDRICK GM – volume: 78 start-page: 281 year: 1983 ident: WOS:A1983QW82300008 article-title: CHELATION OF NICKEL(II) BY CITRATE - THE CRYSTAL-STRUCTURE OF A NICKEL CITRATE COMPLEX, K2[NI(C6H5O7)(H2O)2]2.4H2O publication-title: INORGANICA CHIMICA ACTA-BIOINORGANIC CHEMISTRY contributor: fullname: BAKER, EN – volume: 58 start-page: 243 year: 1982 ident: WOS:A1982NG69300039 article-title: DETERMINATION OF THE COORDINATION-NUMBER AND GEOMETRY OF THE COORDINATION SPHERE OF THE CENTRAL TIN ATOM IN STANNATRANE COMPLEXES BY MOSSBAUER-SPECTROSCOPY publication-title: INORGANICA CHIMICA ACTA-ARTICLES contributor: fullname: KORECZ, L – start-page: 3705 year: 1997 ident: WOS:A1997YD75000009 article-title: Synthesis and characterisation of tin(II) and tin(IV) citrates publication-title: JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS contributor: fullname: Deacon, PR – volume: 71 start-page: 1247 year: 1941 ident: WOS:000081630000012.3 publication-title: J AM CHEM SOC contributor: fullname: BATES RG – volume: 1 start-page: 74 year: 1994 ident: WOS:000081630000012.24 publication-title: TRENDS ORGANOMET CHE contributor: fullname: TIEKINK ERT – volume: 275 start-page: 43 year: 1984 ident: WOS:A1984TQ66500007 article-title: THE C-13 AND SN-119 NMR-SPECTRA OF SOME 4-COORDINATE AND 5-COORDINATE TRI-NORMAL-BUTYLTIN(IV) COMPOUNDS publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: NADVORNIK, M – volume: 30 start-page: 440 year: 1992 ident: WOS:A1992HR29400015 article-title: SOLID-STATE C-13 AND H-1-NMR STUDY OF ANOMALOUS ACID SALTS OF DIBASIC CARBOXYLIC-ACIDS publication-title: MAGNETIC RESONANCE IN CHEMISTRY contributor: fullname: MERWIN, LH – volume: 54 start-page: 750 year: 1998 ident: WOS:000074825000022 article-title: 2[(C6H11)(2)NH2](+)center dot[Sn(O2CCH2CH2CO2)-(C4H9)(3)](-)center dot 1/2(O2CCH2CH2CO2)(2-)center dot H2O, an organostannate consisting of linear polyanionic tributyl(succinato)stannate chains hydrogen bonded into layers by a [tetrakis(dicyclohexylammonium) succinate dihydrate] dicationic network publication-title: ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY contributor: fullname: Ng, SW – volume: 390 start-page: 19 year: 1990 ident: WOS:A1990DQ80900003 article-title: SYNTHESIS OF TRIORGANOSTANNATE ESTERS OF DICARBOXYLIC-ACIDS - CRYSTAL-STRUCTURE OF BIS(DICYCLOHEXYLAMMONIUM) TRISOXALATOTETRAKIS(TRI-NORMAL-BUTYLSTANNATE) .2 ETHANOL publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: NG, SW – volume: 5 start-page: 1 year: 1991 ident: WOS:A1991EW37800001 article-title: STRUCTURAL CHEMISTRY OF ORGANOTIN CARBOXYLATES - A REVIEW OF THE CRYSTALLOGRAPHIC LITERATURE publication-title: APPLIED ORGANOMETALLIC CHEMISTRY contributor: fullname: TIEKINK, ERT – volume: 430 start-page: 139 year: 1992 ident: WOS:A1992JB76000002 article-title: DICYCLOHEXYLAMMONIUM (DICARBOXYLATO)TRIORGANOSTANNATES - CRYSTAL-STRUCTURE OF BIS(DICYCLOHEXYLAMMONIUM) TRIS(MALONATO)TETRAKIS(TRIBUTYLSTANNATE) publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: NG, SW – volume: 62 start-page: 279 year: 1997 ident: WOS:A1997WM58200012 article-title: Synthesis and infrared and H-1,C-13, Sn-119 NMR spectra of some tris- and bis(1-butyl)tin(IV) naphthoates and hydroxynaphthoates publication-title: COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS contributor: fullname: Holecek, J – volume: 55 year: 1999 ident: WOS:000081630000012.17 publication-title: ACTA CRYSTALLOGR S C contributor: fullname: NG SW – start-page: 2735 year: 1991 ident: WOS:A1991GK05900036 article-title: ANTIMONY(III) COMPLEXES WITH CARBOXYLIC-ACIDS .2. PREPARATION AND CRYSTAL-STRUCTURES OF [SB2AG2(C6H6O7)4] AND [SBNA(C6H6O7)2(H2O)2].H2O [C6H6O7 = CITRATE (2-)] publication-title: JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS contributor: fullname: HARTLEY, DW – volume: 46 start-page: 467 year: 1990 ident: WOS:A1990DJ92700008 article-title: PHASE ANNEALING IN SHELX-90 - DIRECT METHODS FOR LARGER STRUCTURES publication-title: ACTA CRYSTALLOGRAPHICA SECTION A contributor: fullname: SHELDRICK, GM – volume: 21 start-page: 3760 year: 1982 ident: WOS:A1982PJ85700032 article-title: 3-POINT ATTACHMENT OF CITRATE TO A COBALT(III) TETRAAMINE COMPLEX publication-title: INORGANIC CHEMISTRY contributor: fullname: JOB, R – start-page: 643 year: 1976 ident: WOS:A1976BP19600017 article-title: ADDITIVE MODEL FOR SN-119 MOSSBAUER QUADRUPOLE SPLITTING IN 5-COORDINATE ORGANOTIN(IV) COMPOUNDS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS contributor: fullname: BANCROFT, GM |
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Snippet | Six tributylstannyl citrates and three tributylstannyl propane-1,2,3-tricarboxylates of the formula (RC)-C-1(CH2COOR2)(COOR3)(CH2COOR4) (R-1 = OH or H, R-2,... |
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SubjectTerms | Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
Title | Infrared, Sn-119, C-13 and H-1 NMR, Sn-119 and C-13 CP/MAS NMR and Mossbauer spectral study of some tributylstannyl citrates and propane-1,2,3-tricarboxylates |
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