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Triorganotin(IV) esters of 2-{[N-(2-oxo-2H-naphthalene-1-yliden)hydrazo]}benzoic acid, instability of the cyclohexyl derivative
Authors: Chalupa Jan | Dušek Libor | Padělková Zdeňka | Švec Petr | Pejchal Vladimír | Růžička Aleš
Year: 2009
Type of publication: článek v odborném periodiku
Name of source: Journal of Coordination Chemistry
Publisher name: Taylor & Francis Ltd.
Place: Abingdon
Page from-to: 1525-1535
Titles:
Language Name Abstract Keywords
cze Triorganotin(IV) esters of 2-{[N-(2-oxo-2H-naphthalene-1-yliden)hydrazo]}benzoic acid, instability of the cyclohexyl derivative? Tři triorganocíničité estery 2-{[N-(2-oxo-2H-naphthalen-1-yliden)hydrazo]}benzoové kyseliny byly připraveny a studovány pomocí IR a NMR spectroskopie a X-ray krystalografie pro tributyl- a triethylcín(IV)-2-{[N-(2-oxo-2H-naphthalen-1-yliden)hydrazo]}benzoatů (2, 3). Tyto sloučeniny jsou monomerní v roztoku se čtyř koordinovaným atomem cínu. Hydrazo tautomerní formy jsou přítomny v chloroformu tak jako v pevné fázi. Koordinační geometrie cínu v 2 a 3 jsou trigonálně bipyramidální. Výtěžek tricyclohexylcíničitého derivátu (4) je mnohem nižší než u 2 či 3, s nestabilitou vůči vlhkosti v roztoku. Produkt reakce s vodou je bis(2-hydroxo)-bis{2-{[N-(2-oxo-2H-naphthalen-1-yliden)hydrazo]}benzoato}tetracyklohexyldicíničitý (4a) dimer triorganocíničité estery;azoidy;NMR;XRD
eng Triorganotin(IV) esters of 2-{[N-(2-oxo-2H-naphthalene-1-yliden)hydrazo]}benzoic acid, instability of the cyclohexyl derivative Three triorganotin(IV) esters of 2-{[N-(2-oxo-2H-naphthalene-1-yliden)hydrazo]}benzoic acid were prepared and studied by IR and NMR spectroscopy and X-ray crystallography for the tributyl- and triethyltin(IV)-2-{[N-(2-oxo-2H-naphthalene-1-yliden)hydrazo]}benzoates (2, 3). These compounds are monomeric in solution with four-coordinate tin. The hydrazo tautomeric forms are present in chloroform solution as well as in the solid state. The coordination geometries of tin in 2 and 3 are trigonal bipyramidal with all three carbons in equatorial positions, one carboxylic oxygen and the quinone-type oxygen from adjacent molecules are in axial positions forming centrosymmetric dimers with the ring containing 20 members. The yield of the tricyclohexyltin(IV) derivative (4) is much lower than 2 or 3, with instability towards moisture in solution. The product of the reaction with water is the bis(2-hydroxo)-bis{2-{[N-(2-oxo-2H-naphthalene-1-yliden)hydrazo]}benzoato}tetracyclohexylditin (4a) dimer. triorganotin(IV) esters; Azodye; NMR; X-ray

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