IR and 13C, 17O, and 119Sn NMR spectra of some bis(1-butyl)tin(IV) carboxylates of dicarboxylic acids

1991 ◽  
Vol 56 (9) ◽  
pp. 1908-1915 ◽  
Author(s):  
Jaroslav Holeček ◽  
Antonín Lyčka ◽  
Milan Nádvorník ◽  
Karel Handlíř
Keyword(s):  
Infrared Spectroscopy ◽  
Nmr Spectroscopy ◽  
Dicarboxylic Acid ◽  
Nmr Spectra ◽  
Dicarboxylic Acids ◽  
119Sn Nmr ◽  
Carboxylic Groups ◽  
Cyclic Oligomers ◽  
The Media ◽  
Oxygen Atoms

Infrared spectroscopy and multinuclear (13C, 17O, and 119Sn NMR spectroscopy have been used to study the structure of bis(1-butyl)tin(IV) carboxylates of dicarboxylic acids (1-C4H9)2. Sn(X(COO)2), where X = (CH2)n (n = 0-8), CH=CH (cis and trans) and C6H4 (ortho and para).The crystalline compounds are formed by linear or cyclic oligomers or polymers whose basic building units represent a grouping composed of the central tin atom substituted by two 1-butyl groups and coordinated with both oxygen atoms of two anisobidentate carboxylic groups derived from different molecules of a dicarboxylic acid. The environment of the tin atom has a shape of a trapezoidal bipyramid. When dissolvet in non-coordinating solvents, the compounds retain the oligomeric character with unchanged structure of environment of the central tin atom. In the media of coordinating solvents the bis(1-butyl)tin(IV) carboxylates of dicarboxylic acids form complexes whose central hexacoordinated tin atom binds two molecules of the solvent trough their donor atoms. Carboxylic groups form monodenate linkages in these complexes.

Study of structure of bis(triphenylstannyl) chromate(VI) by infrared, Mössbauer, and 1H, 13C and 119Sn NMR spectra

1984 ◽  
Vol 49 (6) ◽  
pp. 1497-1504 ◽  
Author(s):  
Karel Handlíř ◽  
Jaroslav Holeček ◽  
Milan Nádvorník ◽  
Antonín Lyčka ◽  
Milan Hucl
Keyword(s):  
Solid State ◽  
Molecular Complex ◽  
Equatorial Plane ◽  
Nmr Spectra ◽  
Three Dimensional ◽  
119Sn Nmr ◽  
Bridge Oxygen ◽  
The Common ◽  
Ester Molecule ◽  
Oxygen Atoms

The infrared, Mössbauer, and 1H, 13C and 119 Sn NMR spectra have been used to study the structure of bis(triphenylstannyl) chromate(VI) in solid state and in solvents of both noncoordinating and coordinating types. In solid state the compound forms a three-dimensional polymer: the tetrahedral CrO4 group and trans-trigonally bipyramidal (C6H5)3SnO2 grouping are connected mutually symmetrically by bridges represented by the common oxygen atoms. The three phenyl groups in the (C6H5)3SnO2 grouping are located in the equatorial plane of the trigonal bipyramide which is completed by two bridge oxygen atoms in axial positions. Solutions in noncoordinating solvents contain monomeric bis(triphenylstannyl) chromate(VI). The ester molecule contain two tetrahedral, (C6H5)3SnO groups bound by oxygen bridges to a CrO4 group which shows the C2v symmetry. In coordinating solvents the title compound forms a molecular complex having the coordination number 5 at the central tin atom.

Synthesis and Infrared and 1H, 13C, 119Sn NMR Spectra of Some Tris- and Bis(1-butyl)tin(IV) Naphthoates and Hydroxynaphthoates

1997 ◽  
Vol 62 (2) ◽  
pp. 279-298 ◽  
Author(s):  
Jaroslav Holeček ◽  
Milan Nádvorník ◽  
Karel Handlíř ◽  
Vladimír Pejchal ◽  
Radovan Vítek ◽  
...  
Keyword(s):  
Nmr Spectra ◽  
Molecular Complexes ◽  
Monomeric Unit ◽  
Hydroxyl Groups ◽  
Carboxylic Group ◽  
Chelate Complexes ◽  
119Sn Nmr ◽  
Carboxylic Groups ◽  
Solvent Molecules

The synthesis and structure of tris(1-butyl)tin(IV) and bis(1-butyl)tin(IV) 1-naphthoates, 2-naphthoates, 1-hydroxy-2-naphthoates, 2-hydroxy-1-naphthoates, 3-hydroxy-2-naphthoates as well as the groups of the corresponding tetrakis(1-butyl)dinaphthoato- and tetrakis(1-butyl)bis(hydroxynaphthoato)distannoxanes have been studied in solutions of both coordinating and noncoordinating solvents by means of infrared and multinuclear (1H, 13C and 119Sn) NMR spectroscopies. In the solutions of noncoordinating solvents, all the tris(1-butyl)tin(IV) compounds are present as isolated monomeric molecules with pseudotetrahedral environment of the central tin atom, or as strongly deformed cis-trigonally bipyramidal chelate complexes with anisobidentate carboxylic group. The bis(1-butyl)tin(IV) compounds form molecular pseudooctahedral complexes with chelate anisobidentate carboxylic groups of naphthoate or hydroxynaphthoate ligands. The (1-butyl)chlorotin(IV) compounds are molecular complexes containing a chelate-bound carboxylic group, their tin atom having a pentacoordinated environment of the bond partners. The tetrakis(1-butyl)dinaphthoato- and tetrakis(1-butyl)bis(hydroxynaphthoato)distannoxanes form dimeric molecular complexes with two pentacoordinated tin atoms and two hexacoordinated ones. In solutions of a coordinating solvent (hexadeuteriodimethyl sulfoxide), the tris(1-butyl)tin(IV) compounds form trans-trigonally bipyramidal complexes with one molecule of the solvent, whereas the bis(1-butyl)tin(IV) and bis(1-butyl)chlorotin(IV) compounds form trapezoidally bipyramidal complexes with two molecules of the solvent. The dimeric tetrakis(1-butyl)bis(hydroxynaphthoato)distannoxanes are monomerized by coordinating solvent, each monomeric unit adding two solvent molecules per one tin atom. The environment of the tin atom is then pseudooctahedral. The hydroxyl groups of naphthoate systems do not take part in any bonds to the tin atom in any of the compounds studied.

Borkomplexe mit Dicarbonsäuren: Bis(oxalato)borate und Bis(malonato)borate/Boron Complexes with Dicarboxylic Acids: Bis(oxalato)borates and Bis(malonato)borates

1982 ◽  
Vol 37 (8) ◽  
pp. 1020-1025 ◽  
Author(s):  
Eberhard Bessler ◽  
Johann Weidlein
Keyword(s):  
Boric Acid ◽  
Dicarboxylic Acid ◽  
Vibrational Spectra ◽  
Nmr Spectra ◽  
Heterogeneous Reaction ◽  
Dicarboxylic Acids ◽  
Continuous Separation ◽  
Boron Complexes

Abstract Several bis(oxalato)borates and bis(malonato)borates have been prepared in heterogeneous reaction from boric acid, dicarboxylic acid and dicarboxylic salt by refluxing in benzene under continuous separation of water. The compounds were characterized by their IR and 11B NMR spectra. The vibrational spectra of the bis(oxalato)borate are discussed in detail.

Study of the aqueous reactions of K[Pt(DMSO)Cl3] with nitrile ligands and crystal structures of Cl(DMSO)Pt(μ-C4H8NO)2Pt(DMSO)Cl and Cl(DMSO)Pt(μ-C5H10NO)2Pt(DMSO)Cl

1992 ◽  
Vol 70 (9) ◽  
pp. 2476-2484 ◽  
Author(s):  
Fernande D. Rochon ◽  
Radia Boughzala ◽  
Robert Melanson
Keyword(s):  
Infrared Spectroscopy ◽  
Nmr Spectroscopy ◽  
Crystal Structures ◽  
Nmr Spectra ◽  
Neutral Medium ◽  
Trans Position ◽  
Medium Ph ◽  
Bond Lengths ◽  
In Trans ◽  
Aqueous Reactions

The aqueous reactions of K[Pt(DMSO)Cl3] with nitriles were studied in different conditions of pH. At normal pH (≈2.4), the ligands RCN, where R is an alkyl group, produced the yellow complexes Pt(DMSO)(R-CN)Cl2. Infrared spectroscopy suggested cis isomers. The 195Pt NMR spectra of the compounds show a resonance around −3000 ppm. The same reactions in neutral medium (pH adjusted to ~7 with NaOH) produced acetamido-bridged dimers (DMSO)ClPt(μ-RCONH)2Pt(DMSO)Cl with all the ligands studied: propionitrile, butyronitrile, dimethylacetonitrile, trimethylacetonitrile, fluoroacetonitrile, chloroacetonitrile, bromoacetonitrile, and dibromoacetonitrile. The results of 195Pt NMR spectroscopy show a head-to-tail isomer, since only one signal around −2750 ppm is observed for each complex. These dimeric compounds are all blue or green depending on the ligand. The same dimers are obtained with all the haloacetonitrile ligands when the pH is not adjusted (≈2.4). The crystal structures of Cl(DMSO)Pt(μ-C4H8NO)2Pt(DMSO)Cl (1) and Cl(DMSO)Pt(μ-C5H10NO)2Pt(DMSO)Cl (2) were determined. The results confirm that the dimers are head-to-tail isomers with the DMSO ligands located in trans position to the O-acetamido atoms. The two crystals belong to the Pna21 space group with a = 11.112(4), b = 20.414(9), c = 10.161(4) Å for 1 and a = 11.607(6), b = 20.113(11), and c = 10.641(5) Å for 2. The structures were refined to R = 0.054 for 1 and R = 0.056 for 2. The Pt—Cl bond lengths are 2.328(10), 2.293(10) Å for 1 and 2.317(9), 2.317(10) Å for 2, while the Pt—S bond lengths are 2.173(10), 2.193(10) for 1 and 2.180(9), 2.176(9) Å for 2. The Pt—O bonds vary from 1.91(2) to 2.08(2) and the Pt—N from 1.88(2) to 2.03(2) Å. The dihedral angle between the two Pt(II) planes is 36°.

17O and 13C NMR spectra of some geminal diacetates

1988 ◽  
Vol 53 (3) ◽  
pp. 588-592 ◽  
Author(s):  
Antonín Lyčka ◽  
Josef Jirman ◽  
Jaroslav Holeček
Keyword(s):  
13C Nmr ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
The Other ◽  
13C Nmr Spectra ◽  
Other Hand ◽  
Carboxylic Esters ◽  
C Nmr ◽  
Oxygen Atoms

The 17O and 13C NMR spectra of eight geminal diacetates RCH(O(CO)CH3)2 derived from simple aldehydes have been measured. In contrast to the dicarboxylates R1R2E(O(CO)R3)2, where E = Si, Ge, or Sn, whose 17O NMR spectra only contain a single signal, and, on the other hand, in accordance with organic carboxylic esters, the 17O NMR spectra of the compound group studied always exhibit two well-resolved signals with the chemical shifts δ(17O) in the regions of 183-219 ppm and 369-381 ppm for the oxygen atoms in the groups C-O and C=O, respectively.

17O, 13C, and 29Si NMR spectra of some acyloxy- and diacetoxysilanes and acetoxygermanes

1986 ◽  
Vol 51 (11) ◽  
pp. 2582-2589 ◽  
Author(s):  
Antonín Lyčka ◽  
Jaroslav Holeček ◽  
Karel Handlíř ◽  
Josef Pola ◽  
Václav Chvalovský
Keyword(s):  
Periodic System ◽  
Time Scale ◽  
Nmr Spectra ◽  
Group Element ◽  
29Si Nmr ◽  
Carboxyl Group ◽  
29Si Nmr Spectra ◽  
Oxygen Atoms

The 17O, 13C, and 29Si NMR spectra of (CH3)3SiOC(O)R, CH3(XCH2)Si(OC(O)CH3)2, and R3GeOC(O)CH3 compounds are reported. In the 17O NMR spectra at 350 K the only signal is observed with the two latter series, but two well-resolved signals are displayed with the (CH3)3SiOC(O)R compounds. The equivalence of both oxygen atoms in carboxyl group on the NMR time scale is discussed from the viewpoint of a possible coordination of the oxygen atoms to the IVB group element of the periodic system.

NMR spectroscopic investigation of p-substituted 2,4,4,6-tetraphenyl-1,4-dihydropyridines and their oxa and thia analogues

1989 ◽  
Vol 54 (7) ◽  
pp. 1854-1869 ◽  
Author(s):  
Marián Schwarz ◽  
Petr Trška ◽  
Josef Kuthan
Keyword(s):  
Nmr Spectroscopy ◽  
Trifluoroacetic Acid ◽  
Spectroscopic Investigation ◽  
Nmr Spectra ◽  
Dynamic Equilibrium

The 1H, 13C and 19F NMR spectra of photochromic p-substituted 2,4,4,6-tetraphenyl-1,4-dihydropyridines IIa-IIg, 1-methyl-2,4,4,6-tetraphenyl-1,4-dihydropyridines IIIa-IIIg, 2,4,4,6-tetraphenyl-4H-pyrans IVa-IVh, and 2,4,4,6-tetraphenyl-4H-thiopyran V were inspected; it was found that compounds IIa-IIg occur in a dynamic equilibrium with their dihydro tautomer VIa-VIg. Also deuteriodeprotonation of IIa and IIIa and their reaction with trifluoroacetic acid were investigated by NMR spectroscopy.

119Sn, 13C and 1H NMR Spectra of Tris(1-butyl)stannyl D-Glucuronate

1997 ◽  
Vol 62 (8) ◽  
pp. 1169-1176 ◽  
Author(s):  
Antonín Lyčka ◽  
Jaroslav Holeček ◽  
David Micák
Keyword(s):  
Chemical Shift ◽  
Carbonyl Group ◽  
1H Nmr ◽  
Equatorial Plane ◽  
Title Compound ◽  
Nmr Spectra ◽  
Hydroxyl Groups ◽  
Carboxylic Group ◽  
H Nmr ◽  
Oxygen Atoms

The 119Sn, 13C and 1H NMR spectra of tris(1-butyl)stannyl D-glucuronate have been measured in hexadeuteriodimethyl sulfoxide, tetradeuteriomethanol and deuteriochloroform. The chemical shift values have been assigned unambiguously with the help of H,H-COSY, TOCSY, H,C-COSY and 1H-13C HMQC-RELAY. From the analysis of parameters of 119Sn, 13C and 1H NMR spectra of the title compound and their comparison with the corresponding spectra of tris(1-butyl)stannyl acetate and other carboxylates it follows that in solutions of non-coordinating solvents (deuteriochloroform) the title compound is present in the form of more or less isolated individual molecules with pseudotetrahedral environment around the central tin atom and with monodentately bound carboxylic group. The interaction of tin atom with oxygen atoms of carbonyl group and hydroxyl groups of the saccharide residue - if they are present at all - are very weak. In solutions in coordinating solvents (hexadeuteriodimethyl sulfoxide or tetradeuteriomethanol), the title compound forms complexes with one molecule of the solvent. Particles of these complexes have a shape of trigonal bipyramid with the 1-butyl substituents in equatorial plane and the oxygen atoms of monodentate carboxylic group and coordinating solvent in axial positions.

Unusual Rearrangement of Naphthalene in the Synthesis of a Novel B8-B8-Bridged Derivative in the [(1,2-C2B9H11)2-3-Co]- Series. X-Ray Structure and 11B NMR Spectra of [8,8'-μ-(CH2-C9H6)-(1,2-C2B9H10)2-3-Co]- (CH3)4N+

1997 ◽  
Vol 62 (5) ◽  
pp. 746-751 ◽  
Author(s):  
Andreas Franken ◽  
Jaromír Plešek ◽  
Christiane Nachtigal
Keyword(s):  
Nmr Spectroscopy ◽  
Single Crystal ◽  
Nucleophilic Substitution ◽  
Nmr Spectra ◽  
X Ray Diffraction ◽  
X Ray ◽  
Unusual Rearrangement ◽  
Multinuclear Nmr Spectroscopy ◽  
11B Nmr ◽  
Isolated Compound

On treatment of the [(1,2-C2B9H11)2Co]- ion with naphthalene in presence of AlCl3 a remarkably bridged [8,8'-μ-(CH2-C9H6)-(1,2-C2B9H10)2-3-Co]- ion is obtained as a single isolated compound. The triatomic -CH2-C9H6- bridge is derived from the rearranged naphthalene nucleus. The mechanism of this reaction is obscure but it does resemble the "Electrophile-Induced Nucleophilic Substitution" reported earlier. The structure of the compound was established by multinuclear NMR spectroscopy and by single crystal X-ray diffraction.

Ribosylierung mono- und bicyclischer Dicarbonsäureimide / Ribosylation of Mono- and Bicyclic Dicarboxylic Acid Imides

1988 ◽  
Vol 43 (5-6) ◽  
pp. 397-402
Author(s):  
Kurt-Peter Raezke ◽  
Hermann Frister ◽  
Eckhard Schlimme
Keyword(s):  
Nmr Spectroscopy ◽  
Dicarboxylic Acid ◽  
Phthalic Acid ◽  
Cyclic Imides ◽  
Tin Tetrachloride

The N-trimethylsilyl compounds of the cyclic imides derived from cis-cyclohexan-1,2-dicarboxylic acid, cis-4-cyclohexen-1,2-dicarboxylic acid and phthalic acid were prepared. Reaction of the N-silylated cyclic imides 2 and 10 with 1,2,3,5-tetra-O-acetyl-β-ᴅ-ribofuranose in the presence of tin tetrachloride yielded the appropriate unusual ribonucleosides 4 and 12 whereas 14 led only to traces of the ribosylated derivative. The silylation and ribosylation sites in the aforementioned bicyclic imides were proved by 1H, 13C, and 29Si NMR spectroscopy and compared with data found for the monocyclic imides N-succinimide and N-maleinimide.

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