Synthesis and characterization of some tin(II) and tin(IV) derivatives of 4-acyl-5-pyrazolones. Crystal structure of bis(1-phenyl-3-methyl-4-acetyl-pyrazolon-5-ato)tin(II)

Pettinari, Cláudio; Marchetti, Fábio; Cingolani, Antonella; Marciante, C.; Spagna, R.; Colapietro, Marcello

doi:10.1016/s0277-5387(00)83014-4

Cited by 26 publications

(17 citation statements)

References 32 publications

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“…The O1ϪSnϪO51 angle of 89.2(3)°also shows significant deviation from the ideal value of 120°due to the lone pair. This structure is similar to that of bis(4-acetyl-3-methyl-1-phenylpyrazolon-5-ato)tin(), which has been determined crystallographically both as the pure complex [40] and as a methanol solvate, [54] although neither shows a twofold axis as for 6. The structural parameters in the coordination sphere of all three structures are similar, as shown in Table 5.…”

Section: Hqsupporting

confidence: 63%

“…In 1994 we synthesized some tin() acylpyrazolonates [40] and found that these compounds are more stable than analogous tin() derivatives of classical β-diketonates. [16,41Ϫ43] Here we report a systematic investigation of the interaction of tin() with acylpyrazolonates to determine if variation of steric and electronic features of acylpyrazolones can affect the solid-state and solution structures of tin() compounds.…”

Section: Figure 1 Q Proligands Used In This Workmentioning

confidence: 99%

“…[52,56,57] Table 5. X-ray structural parameters in the coordination sphere of bis(4-acyl-5-pyrazolon-5-ato)tin() [40] methanol solvate [54] The IR spectrum of 18 shows several absorption bands in the metalϪcarbonyl stretching region at ν ϭ 2059, 1947 and 1880 cm…”

Section: Hqmentioning

confidence: 99%

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Tin(II) and Lead(II) 4‐Acyl‐5‐pyrazolonates: Synthesis, Spectroscopic and X‐ray Structural Characterization

et al. 2004

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Novel tin(II) β‐diketonate Sn(Q)2 complexes [HQ = 1‐R1‐3‐R3‐4‐R4(C=O)‐pyrazol‐5‐one; HQC: R1 = Ph, R3 = Me, R4 = Cy; HQS: R1 = Ph, R3 = Me, R4 = CHPh2; HQL: R1 = Ph, R3 = Me, R4 = CH2Ph; HQT: R1 = Ph, R3 = Me, R4 = CH2tBu; HQE: R1 = Ph, R3 = Me, R4 = Et; HQB: R1 = Ph, R3 = Me, R4 = tBu; HQW: R1 = Ph, R3 = Me, R4 = p‐(tBu)Ph; HQR: R1 = Ph, R3 = Me, R4 = p‐[(CH2)5CH3]Ph; HQN: R1 = p‐NO2Ph, R3 = Me, R4 = Ph; HQM: R1 = Me, R3 = Me, R4 = Ph; HQD: R1 = Me, R3 = Me, R4 = Me; HQP: R1 = Ph, R3 = Ph, R4 = Ph; HQG: R1 = Ph, R3 = Ph, R4 = Me; HQF: R1 = p‐CF3Ph, R3 = Me, R4 = Ph; HQH: R1 = p‐CF3Ph, R3 = Me, R4 = Me] have been isolated and characterized by single‐crystal X‐ray diffraction analyses, IR, 1H, 13C, 119Sn NMR and 119Sn Mössbauer spectroscopy, ESI mass spectrometry, conductivity and molecular weight measurements. The tin complexes SnQ2 are air‐stable, contrary to equivalent compounds of classical β‐diketones, and adopt mononuclear pseudo‐trigonal‐bipyramidal structures (pSnO4, where p is a stereochemically active lone electron pair) in which both ligands chelate a single metal center, as confirmed in the X‐ray crystal structure of Sn(QL)2. This structure fits a trend for all “SnO4” compounds: Sn−O(primary) and Sn−O(secondary) bonds are associated with small O(primary)−Sn−O(primary) and wide O(secondary)−Sn−O(secondary) bond angles. The reactivity of Sn(QT)2 toward RI (R = Me or Et) and CrCO6 has been investigated. The compounds PbQ2 (HQ = HQT, HQB, HQW, HQD) have been also synthesized and the X‐ray structures of Pb(QB)2 and Pb(QT)2 in the solid state determined. These are different from SnQ2 and are composed of “PbO4” moieties with additional interactions from neighboring units to produce polymeric forms. Compound Pb(QT)2 is unusual in having the metal−O(pyrazolonato) bond longer than the metal−O(acyl) one, probably due to a Pb−arene interaction with a neighboring phenyl ring. The sterically less hindered Pb(QD)2 reacts with phen (1,10‐phenanthroline) yielding the mixed ligand complex [Pb(QD)2(phen)]. In this work, in addition to the different coordination numbers expressed by Sn and Pb, associated with the larger covalent radius of the latter, the binding mode of 4‐acyl‐5‐pyrazolonates to Pb is syn whereas for Sn it is anti. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Section: Hqsupporting

confidence: 63%

Section: Figure 1 Q Proligands Used In This Workmentioning

confidence: 99%

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Tin(II) and Lead(II) 4‐Acyl‐5‐pyrazolonates: Synthesis, Spectroscopic and X‐ray Structural Characterization

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“…3)] and their organotin(IV) derivatives have been reported elsewhere. [10][11][12] The fungicidal and insecticidal activities of these compounds have been determined according to standard procedures in the literature, as described in the Experimental section. 4,14 …”

Section: Resultsmentioning

confidence: 99%

“…5 The molecular structures of many more diorganotin(IV) derivatives of the same ligand have been published recently. [10][11][12] We have also described the molecular structure of the first triorganotin(IV) derivative elsewhere. 13 Hence, this study was commenced to investigate the possible fungicidal and insecticidal activities of 4-acetyl-(HPMAP) and 4-benzoyl-3-methyl-1-phenylpyrazol-5-ones (HPMBP) and their di-and tri-organotin(IV) derivatives, and to correlate any possible role of the coordination environment around tin, as well as stability factors, with the observed bioactivities.…”

Section: Introductionmentioning

confidence: 99%

Correlation of Coordination Geometries and Stability Factors in Organotin(IV) Derivatives of 4-Acylpyrazol-5-onates with their Fungicidal (Mycelial Control) and Insecticidal (Topical Toxicity, Larvicidal and Ovicidal) Activities

Omotowa

Mesubi

1997

Appl. Organometal. Chem.

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A Novel Configuration of a Benzoylacetonato-Diorganotin Species is Modified by an Electron-Withdrawing Substituent on Tin − Synthesis, IR and NMR Spectroscopy, Structure, and ab initio Studies

Pettinari

Marchetti

Pettinari

et al. 2002

Eur. J. Inorg. Chem.

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Keywords: Tin / O ligands / NMR spectroscopy / Crystal structure / Ab initio calculationsDiorganotin(IV) complexes of the β-diketonato benzoylacetonato ligand were synthesized and characterized with IR and multinuclear (H, C, Sn) NMR spectroscopy. The X-ray diffraction study of bis(benzoylacetonato)di-tert-butyltin(IV) shows two independent molecules in the crystallographic unit cell. The metal polyhedron is a distorted octahedral (Skewed Trapezoidal Bipyramidal) with the trans angle C−Sn−C of 151.5(5)°. Each ligand chelates the metal with different donor abilities [Sn−O bond lengths of 2.423(8) Å and 2.135(8) Å in one ligand, and 2.107(9) Å and 2.357(8) Å in the other]; results for the 2nd molecule are similar. The coordination arrangement differs from those of related bis(β-diketonato)diorganotin derivatives containing asymmetric ligands, which are characterized by an approximate C s symmetry, in that both benzoylacetonato ligands point their methyl (and phenyl) substituents across (anti) the metal atom. Chelate planarity and some phenyl-chelate coplanarity was observed. Hartree−Fock (HF) and Density Functional Theory (DFT) calculated structures are in good [a]

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Synthesis and characterization of some tin(II) and tin(IV) derivatives of 4-acyl-5-pyrazolones. Crystal structure of bis(1-phenyl-3-methyl-4-acetyl-pyrazolon-5-ato)tin(II)

Cited by 26 publications

References 32 publications

Tin(II) and Lead(II) 4‐Acyl‐5‐pyrazolonates: Synthesis, Spectroscopic and X‐ray Structural Characterization

Tin(II) and Lead(II) 4‐Acyl‐5‐pyrazolonates: Synthesis, Spectroscopic and X‐ray Structural Characterization

Correlation of Coordination Geometries and Stability Factors in Organotin(IV) Derivatives of 4-Acylpyrazol-5-onates with their Fungicidal (Mycelial Control) and Insecticidal (Topical Toxicity, Larvicidal and Ovicidal) Activities

A Novel Configuration of a Benzoylacetonato-Diorganotin Species is Modified by an Electron-Withdrawing Substituent on Tin − Synthesis, IR and NMR Spectroscopy, Structure, and ab initio Studies

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