C,N‐chelated triorganotin(IV) diesters of 4‐ketopimelic acid and their fungicidal activity

Chalupa, Jan; Handlíř, Karel; Padělková, Zdeňka; Vejsová, Marcela; Buchta, Vladimı́r; Jirásko, Robert; Růžička, Aleš

doi:10.1002/aoc.1391

Cited by 12 publications

(7 citation statements)

References 40 publications

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“…The presence of particular groups can be associated with the typical neutral losses, such as hydrogen halide for the presence of halogen, the loss of carbon dioxide for organometallic carboxylates, the loss of alkene or alkane in the presence of alkyl substituents on the metal atom or other ring structures, the loss of 28 (N 2 ) confirms the presence of an azo group in the molecule, etc. For organometallic compounds that contain two or more alkyl/aryl substituents, cleavages of these bonds that result in subsequent neutral losses of alkene and alkane for the alkyl substitution (Baul et al, 2005a(Baul et al, , 2006a(Baul et al, , 2008Chalupa et al, 2006Chalupa et al, , 2008Jirásko et al, 2007), Ru and Si (Kriesel et al, 1998) Sn (Carraher & Lanz, 2003;Carraher & Morie, 2004;Carraher et al, 2007) Sn and Si (Schumann et al, 2006) Ti and Si (Arevalo et al, 2001) MALDI QqTOF…”

Section: Tandem Mass Spectra Of Organometallic Compoundsmentioning

confidence: 99%

“…Bu, butyl; Ph, phenyl; Bz, benzyl; Et, ethyl; L, ligand; Cat, cationic part; An, anionic part. cycloalkane and cykloalkene for cykloalkyl (Chalupa et al, 2006), C 6 H 6 and C 6 H 4 (Baul et al, 2006b;Chalupa et al, 2006Chalupa et al, , 2008 for the phenyl substitution or C 7 H 8 , and C 7 H 6 for the benzyl substitution (Baul et al, 2006c;Chalupa et al, 2006Chalupa et al, , 2008Jirásko et al, 2007) are typical. In the case of the presence of some complex ligand on the metal atom, the neutral losses depend on the structures of particular ligands.…”

Section: Cf3so3 Complex Ligandmentioning

confidence: 99%

“…The important point is the development of appropriate chromatographic methods. Gas chromatography combined with inductively coupled plasma time-of-flight mass spectrometry (ICP-MS) enables high sensitivity and resolution, but the time-consuming preparation of volatile derivates is inevitable, and can influence the reproducibility, especially for methyl (Larsen et al, 2001;Mester & Pawliszyn, 1999) 16 CH 4 methyl (Chalupa et al, 2006;Larsen et al, 2001;Pham et al, 2007) 18 H 2 O hydroxyl, carboxylate (Baul et al, 2006d;Baul et al, 2007b;Florencio et al, 1997;Chalupa et al, 2006;Chalupa et al, 2008;Jirásko et al, 2009;Kolářová et al, 2004;Larsen et al, 2001; 28 C 2 H 4 ethyl (Kolářová et al, 2004;Lamb & Sweetman, 1996) CO carbonyl (Baul et al, 2005a;Jirásko et al, 2007;Seiwert & Karst, 2007;Yeo et al, 1999) CO carbene complexes (Crawford et al, 2006;Jiang et al, 2000;KaneMaguire et al, 1996;Martinez-Alvarez et al, 2004;Mastrorilli et al, 2004;Mlýnek & Dahl, 1997;Moret et al, 2005;Thompson et al, 2003) N 2 azo group (Baul et al, 2005b;Baul et al, 2006b) 29 C 2 H 5 .…”

Section: Simple Main-group Organometallic Compoundsmentioning

confidence: 99%

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Structural analysis of organometallic compounds with soft ionization mass spectrometry

Jirásko

Holčapek

2010

Mass Spectrometry Reviews

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The analysis of organometallic compounds with mass spectrometry has some special features in comparison with organic and bioorganic compounds. The first step is the choice of a suitable ionization technique, where the electrospray ionization is certainly the best possibility for most classes of organometallic compounds and metal complexes. Some ionization mechanisms of organometallic compounds are comparable to organic molecules, such as protonation/deprotonation, and adduct formation with sodium or potassium ions; however, in many cases, different mechanisms and their combinations complicate the spectra interpretation. Organometallics frequently undergo various types of adduct and polymerization reactions that result in significantly higher masses observed in the spectra in comparison to molecular weights of studied compounds. Metal elements typically have more natural isotopes than common organic elements, which cause characteristic wide distributions of isotopic peaks; for example, tin has ten natural isotopes. The isotopic pattern can be used for the identification of the type and number of metal elements in particular ions. The ionization and fragmentation behavior also depend on the type of metal atom; therefore, our discussion of mass spectra interpretation is divided according to the different type of organometallic compounds. Among various types of mass spectrometers available on the market, trap-based analyzers (linear or spherical ion-traps, Orbitrap) are suitable to study complex fragmentation pathways of organometallic ions and their adducts, whereas high-resolution and high-mass accuracy analyzers (time-of-flight-based analyzers, or Fourier transform-based analyzers-Orbitrap or ion cyclotron resonance mass spectrometers) provide accurate masses applicable for the determination of the elemental composition of individual ions.

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Section: Tandem Mass Spectra Of Organometallic Compoundsmentioning

confidence: 99%

Section: Cf3so3 Complex Ligandmentioning

confidence: 99%

Section: Simple Main-group Organometallic Compoundsmentioning

confidence: 99%

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Structural analysis of organometallic compounds with soft ionization mass spectrometry

Jirásko

Holčapek

2010

Mass Spectrometry Reviews

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“…Each ring is composed of (eSneAeSneAeSneBeSneAeSneAeSneBe) sequence; where A is the core acid, B is the bridging one and Sn is SnBu 3 moiety. This is in strong contrast with the supramolecular arrangement of triorganotin(IV) carboxylates with a longer chainketopimelic acid [6,7] where only twenty eight-, twentymembered rings or monomeric structures were found. The ring sequence consisted of four alternating terminal and bridging acids between four organotin moieties for the unit with the largest ring.…”

Section: X-ray Crystallographymentioning

confidence: 83%

“…Acetone 1,3-dicarboxylic acid (3-oxopentanedioic acid, HOOCCH 2 C(]O)CH 2 COOH) is a "shorter" analogue of 4-ketopimelic acid [6,7] studied recently. In contrast to 4-ketopimelic acid, acetone 1,3-dicarboxylic acid exists partially in its enol form e HOOCCH]C(eOH)CH 2 COOH.…”

Section: Introductionmentioning

confidence: 99%

Structural study of di- and triorganotin(IV) dicarboxylates containing one double bond

Lyčka

Růžička

Vaněček

et al. 2010

Journal of Organometallic Chemistry

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Structural Diversity of Coordination Cores in Homoleptic Tetraaryltin(IV) Dioxolane, Aldehyde and Imines: The First Octacoordinated Double Helicate Tetraorganotin(IV) Compound

2013

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Reaction of [2‐{(CH2O)2CH}C6H4]Li with SnCl4 in a 4:1 molar ratio afforded [2‐{(CH2O)2CH}C6H4]4Sn (1), which was deprotected to give [2‐(O=CH)C6H4]4Sn (2). Homoleptic [2‐(RN=CH)C6H4]4Sn [R = Me2NCH2CH2 (3), 2,4,6‐Me3C6H2 (4), PhCH2 (5)] were obtained by condensation of 2 with the corresponding amine either in solution or by using a green, solvent‐free procedure for (imino)arylmetal species. All compounds were characterised by multinuclear NMR spectroscopy and mass spectrometry, and their molecular structures were determined by single‐crystal X‐ray diffraction. In all cases, the C4Sn core is distorted tetrahedral as a result of the combined effects of the intramolecular coordination of the heteroatoms from the organic ligands and the steric impediments imposed by the ligands. The overall coordination around tin was found to be different, that is, coordination numbers from six for 1 and 4, to seven for 3 and 5 and eight for 2. Compound 2 is the first example of a mononuclear tetraorganotin(IV) compound that contains an octacoordinated metal centre with a double helicate topology in the solid state. Multinuclear NMR spectroscopy studies in solutions of CDCl3 are consistent with equivalent organic groups attached to a tetracoordinate tin atom.

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C,N‐chelated triorganotin(IV) diesters of 4‐ketopimelic acid and their fungicidal activity

Cited by 12 publications

References 40 publications

Structural analysis of organometallic compounds with soft ionization mass spectrometry

Structural analysis of organometallic compounds with soft ionization mass spectrometry

Structural study of di- and triorganotin(IV) dicarboxylates containing one double bond

Structural Diversity of Coordination Cores in Homoleptic Tetraaryltin(IV) Dioxolane, Aldehyde and Imines: The First Octacoordinated Double Helicate Tetraorganotin(IV) Compound

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