Issue 11, 2001

The interaction of organotin(IV) acceptors with a benzoic acid containing two pyrazolone groups

Abstract

A new polydentate ligand, namely 2-[(5-hydroxy-1-phenyl-3-methylpyrazol-4-yl)(5-oxo-1,5-dihydro-4-phenyl-2-methylpyrazol-4-ylidene)methyl]benzoic acid (H2QBz), has been prepared and characterized. The structure of the ligand H2QBz consists of discrete molecules linked to one another by an extensive H-bonding network. The reactivity of H2QBz towards [R3Sn]2O (R = Ph or Bun) and RnSnCl4 − n (R = Me, Bun, But, Ph, n = 2; R = Me, n = 3) has been investigated. Mono- and di-nuclear derivatives have been obtained depending on the nature of the starting acceptor and reaction conditions. [Ph3Sn(HQBz)] 1 contains the HQBz ligand coordinated to Ph3Sn through the deprotonated carboxylic group. In the complex [(H2O)Ph3Sn(HQBz)] 2, obtained by hydration of 1, the coordination sphere of tin is completed by bonding to a water molecule. The compounds [(R3Sn)2(QBz)] (R = Me, 3; Bun, 4) contain the dianionic ligand bridged to two triorganotin(IV) fragments. In solution the mononuclear triorganotin(IV) aqua complexes [(H2O)R3Sn(HQBz)] (R = Ph, 2; Bun, 5) loose the molecule of water and slowly decompose, yielding the free ligand and the R3SnOH species. The diorganotin(IV) derivatives [R2Sn(QBz)]2 (R = Me, 6; But, 7; Bun, 8; Ph, 9) are dinuclear both in the solid state and in solution. In the structure of [Me2Sn(QBz)]26 both acidic H atoms of the ligand are substituted by tin: a dimeric centrosymmetric structure forms, involving two [QBz]2− ligands acting as bridges between two tin atoms through both pyrazolone and benzoate moieties. Sn centers in the dimer are five-coordinated in a strongly distorted trigonal bypiramidal environment.

Graphical abstract: The interaction of organotin(IV) acceptors with a benzoic acid containing two pyrazolone groups [ ]

Supplementary files

Article information

Article type
Paper
Submitted
29 Jan 2001
Accepted
10 Apr 2001
First published
04 May 2001

J. Chem. Soc., Dalton Trans., 2001, 1790-1797

The interaction of organotin(IV) acceptors with a benzoic acid containing two pyrazolone groups

C. Pettinari, F. Marchetti, R. Pettinari, D. Martini, A. Drozdov and S. Troyanov, J. Chem. Soc., Dalton Trans., 2001, 1790 DOI: 10.1039/B100988P

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements