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Organotin compounds: from kinetics to stereochemistry and antitumour activities

Published on Apr 1, 2005in Applied Organometallic Chemistry 3.26
· DOI :10.1002/aoc.771
Marcel Gielen34
Estimated H-index: 34
(Vrije Universiteit Brussel),
Monique Biesemans34
Estimated H-index: 34
(Vrije Universiteit Brussel),
Rudolph Willem38
Estimated H-index: 38
(Vrije Universiteit Brussel)
Cite
Abstract
An overview is given of the research performed by the authors at the Universite Libre de Bruxelles and Vrije Universiteit Brussel, including the kinetics, stereochemistry and mechanism of SE2 reactions at a saturated carbon atom, the synthesis of chiral organotin compounds and their configurational and optical stability, the fluxionality of trigonal bipyramidal metal atoms and the stereochemistry of SN2 reactions at tetrahedrally substituted P, Si, Ge, Sn atoms, the cytotoxicity of many series of organotin compounds and the structure and reactivity of organotin salicylaldoximate clusters. Copyright © 2005 John Wiley & Sons, Ltd.
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  • Citations (157)
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References99
Newest
Published on Sep 2, 2010in Bulletin des Sociétés Chimiques Belges
Marcel Gielen8
Estimated H-index: 8
(ULB: Université libre de Bruxelles),
Jacques Nasielski9
Estimated H-index: 9
(ULB: Université libre de Bruxelles)
The mass spectra of a series of aryltrimethyltins are described and analysed. The main features are: a relatively weak molecular ion, a very important ArSnMe2+ ion (base peak), a low intensity ArSnMe+ fragment and a non negligible ArSn+ peak. These findings may be related to the well known stable valence states of tin (IVSn and IISn) and the unfavourable IIISn and ISn states. Whereas a methyl group is easier to cleave from the ArSnMe3+ ion than the phenyl radical, n-butyl seems to be more strong...
Published on Sep 2, 2010in Bulletin des Sociétés Chimiques Belges
Marcel Gielen25
Estimated H-index: 25
(ULB: Université libre de Bruxelles),
Hassan Mokhtar-Jamaï4
Estimated H-index: 4
(ULB: Université libre de Bruxelles)
The synthesis of optically active p‐anisyl‐(3‐hydroxy‐3‐methylbutyl)methyl‐α‐naphthyl tin (IV) is described. The spectroscopic properties of this compound and of the products used as synthesis intermediates are given. The two diastereoisomers of (‐)‐menthyl‐β‐(methylnaphthyl‐phenylstannyl)‐propionate (V) could not be separated. Copyright © 1975 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
Published on Sep 2, 2010in Bulletin des Sociétés Chimiques Belges
Stéphane Boué7
Estimated H-index: 7
(ULB: Université libre de Bruxelles),
Marcel Gielen8
Estimated H-index: 8
(ULB: Université libre de Bruxelles),
Jacques Nasielski9
Estimated H-index: 9
(ULB: Université libre de Bruxelles)
The mass spectra of mixed tetraalkyltins are described and analysed. The fragmentation pattern is in agreement with the hypothesis of prefered Sn(IV) and Sn(II) valence states in the tin‐containing fragments. These states are reached by losing an alkyl radical from the next higher unfavourable valence state, or by losing an alkene or alkane molecule from a favourable valence state. The ease of cleavage of a carbon‐tin bond in the molecular ion parallels the stabilization of the leaving alkyl rad...
Published on Sep 2, 2010in Bulletin des Sociétés Chimiques Belges
Stéphane Boué7
Estimated H-index: 7
(ULB: Université libre de Bruxelles),
Marcel Gielen25
Estimated H-index: 25
(ULB: Université libre de Bruxelles)
+ 2 AuthorsRichard Spielmann2
Estimated H-index: 2
(ULB: Université libre de Bruxelles)
Nine new racemic organotin derivatives: MePriPrSnR (R = Br, Et, Bu, iBu, sBu, tBu) and MeiPrcycloHexSnR′ (R′ = Br, Et, anisyl) have been synthesized in high yields. Their mass spectra and those of some intermediates are given and discussed on the basis of previous results. Copyright © 1969 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
Published on Sep 2, 2010in Bulletin des Sociétés Chimiques Belges
Marcel Gielen25
Estimated H-index: 25
(ULB: Université libre de Bruxelles),
Noel Vanlautem1
Estimated H-index: 1
(ULB: Université libre de Bruxelles)
Permutations may be used to describe the transformations of a given complex MLn into one of the n!/hr, possible isomers. The determination of the n! possible permutations gives all the isomerization paths of this complex occuring by nonbond‐rupture mechanisms. This is applied to the case of four; five‐ and six‐ coordinate structures and might be applied as well to higher coordination numbers. Copyright © 1970 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
Published on Sep 2, 2010in Bulletin des Sociétés Chimiques Belges
Marcel Gielen8
Estimated H-index: 8
(Free University of Brussels),
Jacques Nasielski9
Estimated H-index: 9
(Free University of Brussels),
Gilbert Vandendunghen2
Estimated H-index: 2
(Free University of Brussels)
The mass spectra of a series of hexaalkyldimetals are described and discussed. The fragmentation rules available in the literature for organometallic compounds of group IV B are also valid here. The PMR spectra of these derivatives have been recorded and analyzed. Copyright © 1971 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
Marcel Gielen25
Estimated H-index: 25
(ULB: Université libre de Bruxelles),
Jacques Nasielski17
Estimated H-index: 17
(ULB: Université libre de Bruxelles),
J. Topart7
Estimated H-index: 7
(ULB: Université libre de Bruxelles)
Published on Sep 1, 2010in Bulletin des Sociétés Chimiques Belges
Marcel Gielen34
Estimated H-index: 34
(Vrije Universiteit Brussel),
Hassan Mokhtar-Jamaï4
Estimated H-index: 4
(ULB: Université libre de Bruxelles)
The optical stability of methylneophyltrityltin halides is greater than that of less sterically hindered triorganotin halides.
Published on Sep 1, 2010in Bulletin des Sociétés Chimiques Belges
Marcel Gielen34
Estimated H-index: 34
(Free University of Brussels),
Abdelaziz El Khloufi8
Estimated H-index: 8
(Free University of Brussels)
+ 3 AuthorsRudolph Willem38
Estimated H-index: 38
(Free University of Brussels)
Bis(di-n-butyl)(2,3,6-trifluorobenzoato)- and bis(di-n-butyl)(2,3,4,5-tetrafluorobenzoato)tin oxides were synthesized and characterized by 1H, 13C, 19F and 119Sn NMR as well as by 119mSn Mossbauer spectroscopy. They were screened in vitro against six human tumour cell lines. MCF-7 and EVSAT. breast cancers, WiDr, a colon carcinoma, IGROV, an ovarian cancer, M19 MEL, a melanoma and A498, a renal cancer.
Published on Sep 1, 2010in Bulletin des Sociétés Chimiques Belges
Marcel Gielen25
Estimated H-index: 25
(Vrije Universiteit Brussel),
Yves Tondeur6
Estimated H-index: 6
(ULB: Université libre de Bruxelles)
Stannylamines, ‐phosphines and ‐arsines are shown to be configurationally stable within the NMR time‐scale, even in the presence of a strong nucleophile. The configurational stability of triorganotin hydrides and the configurational unstability of triorganotin halide has been checked. Copyright © 1975 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
Cited By157
Newest
Published on Jul 1, 2019in Heliyon
A. Palanimurugan (Government Arts College, Coimbatore), A. Dhanalakshmi (Government Arts College, Coimbatore)+ 1 AuthorsA. Kulandaisamy (Government Arts College, Coimbatore)
Abstract New tetradentate Schiff base transition metal complexes have been derived from salicylidene-4-imino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and histidine were characterized by CHN analysis, magnetic susceptibility measurements, molar conductance, FAB-MS, IR, 1 H-NMR, UV, CV, EPR, Fluorescence emission, AFM and Powder XRD techniques. AFM images and Powder XRD data endure that the complexes are nano-size grains with polycrystalline structure. The spectral evidences showed that all the met...
Published on Feb 16, 2019in Journal of Coordination Chemistry 1.69
Shilpa Kumari (HPU: Himachal Pradesh University), Neeraj Sharma6
Estimated H-index: 6
(HPU: Himachal Pradesh University)
Published on Feb 15, 2019in International Journal of Molecular Sciences 4.18
Enis Nadia Md Yusof3
Estimated H-index: 3
,
Muhammad A. M. Latif1
Estimated H-index: 1
+ 6 AuthorsThahira Begum S. A. Ravoof9
Estimated H-index: 9
Six new organotin(IV) compounds of Schiff bases derived from S-R-dithiocarbazate [R = benzyl (B), 2- or 4-methylbenzyl (2M and 4M, respectively)] condensed with 2-hydroxy-3-methoxybenzaldehyde (oVa) were synthesised and characterised by elemental analysis, various spectroscopic techniques including infrared, UV-vis, multinuclear (1H, 13C, 119Sn) NMR and mass spectrometry, and single crystal X-ray diffraction. The organotin(IV) compounds were synthesised from the reaction of Ph2SnCl2 or Me2SnCl2 ...
Published on Feb 1, 2019in Applied Organometallic Chemistry 3.26
Claudia Huedo (UAM: Autonomous University of Madrid), Franca Zani20
Estimated H-index: 20
+ 3 AuthorsElena López-Torres14
Estimated H-index: 14
(UAM: Autonomous University of Madrid)
Published on Jan 1, 2019in Journal of Organometallic Chemistry 2.07
Khodayar Gholivand19
Estimated H-index: 19
(TMU: Tarbiat Modares University),
Masoumeh Azadbakht1
Estimated H-index: 1
(TMU: Tarbiat Modares University)
+ 2 AuthorsCanan Kazak15
Estimated H-index: 15
(OMU: Ondokuz Mayıs University)
Abstract A series of new bisphosphoramidate and (thio)phosphoramidate derivatives with the general formula R 1 R 2 P(X)–Y–P(X)R 1 R 2 have been synthesized and characterized by IR and NMR spectroscopies ( L 1 – L 12 ). The crystal structure of compound 1,4-[(C 2 H 5 O) 2 P(S)(CH 2 ) 3 NH] 2 C 4 H 8 N 2 ( L 4 ) is also investigated by X-ray diffraction analysis. Two novel organotin(IV) complexes μ-{1,4-[(C 6 H 5 ) 2 P(O)(CH 2 ) 3 NH] 2 C 4 H 8 N 2 }[SnR 3 Cl] 2 , R 3 SnCl (R = phenyl/butyl), C 1 ...
Published on Mar 1, 2018in Applied Organometallic Chemistry 3.26
Mohamed M. El-bendary12
Estimated H-index: 12
(Tanta University),
Safaa El-din H. Etaiw16
Estimated H-index: 16
(Tanta University)
The reaction between aqueous solution of Me3SnCl and acetonitrile solution of quinaldic acid (quinH) at room temperature affords a new organotin complex, [Me3Sn(quinH)(quin)]⋅6H2O (1). Complex 1 was structurally characterized using infrared, UV–visible and NMR spectra, thermogravimetric analysis and single-crystal X-ray analysis. The network structure of 1 is developed by a limitless number of discrete mononuclear molecules forming a one-dimensional chain via hydrogen bonds. Extensive hydrogen b...
Published on Jan 17, 2018in Zeitschrift für anorganische und allgemeine Chemie 1.34
Xiao Xiao , Wenliang Li1
Estimated H-index: 1
+ 2 AuthorsBo Feng3
Estimated H-index: 3
Self-assembly of dibutyltin oxide with 3-(1,3-dioxo-2,3-dihydro-1H-phenalen-2-yl)benzoic acid (HL) produces (n-Bu)2SnL2 (complex 1) when benzene is used as solvent, while the reaction generates {[(n-Bu)2SnO]2L}2·C7H8 (complex 2) when toluene is reactive solvent. The novel organotin carboxylate (n-Bu)2SnL2 (complex 1) was characterized by elemental analysis, IR, 1H, 13C, 119Sn NMR spectroscopy. Single crystal X-ray study reveals that 1 is a dialkyltin carboxylate monomer possessing crystallograph...
Published on Oct 1, 2017in Russian Journal of General Chemistry 0.64
Akhtar Munir3
Estimated H-index: 3
(QAU: Quaid-i-Azam University),
Muhammad Sirajuddin13
Estimated H-index: 13
(University of Science and Technology)
+ 6 AuthorsI. Aziz1
Estimated H-index: 1
(QAU: Quaid-i-Azam University)
Four new organotin (IV) complexes with general formula R3SnL/R2SnL2, where R = CH3, n-C4H9, C6H5 and L = Levofloxacin, were synthesized and characterized by elemental analyses, FT-IR and NMR (1H and 13C) spectroscopy. Spectroscopic data suggested a six-coordinated geometry for diorganotin(IV) derivatives and a five-coordinated geometry for triorganotin(IV) derivatives. The value of Me–Sn–Me bond angle for di- and trimethyltin complexes using the Lockhart equation, were 150° and 116°, respectivel...
Published on Jun 3, 2017in Inorganic and Nano-Metal Chemistry
Taiyu Liu (CPU: China Pharmaceutical University), Jiayang Sun (Henan University)+ 2 AuthorsMingxue Li (Henan University)
ABSTRACTThe diorganotin(IV) complex [Ph2Sn(L)(OAc)]·EtOH (1), where HL = 2-acetylpyridine N4-cyclohexyl thiosemicarbazone, has been synthesized and characterized by elemental analysis, IR, UV–vis, NMR, PL, and mass spectrometry. The crystal structure was characterized by X-ray diffraction method. Tin(IV) ion is coordinated by one L− anion through pyridine nitrogen, azomethine nitrogen and sulfur atom, two phenyl groups, and one OAc− anion through two carboxyl oxygen atoms building a distorted pe...