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Comptes Rendus

X-ray crystal structure and spectral characterization of pseudo five-coordinate Hg(II) polymeric and four-coordinate binuclear complexes of an ambidentate sulfonium ylide
Comptes Rendus. Chimie, Volume 17 (2014) no. 12, pp. 1257-1263.

Abstract

The reaction of ambidentate sulfonium ylide (Me)2SCHC(O)C6H4-p-OCH3(Y) with HgX2 [X = Cl (1), Br (2) and I (3)] in equimolar ratios using methanol as the solvent leads to two types of products. Single-crystal X-ray diffraction analysis reveals (i) a two-dimensional polymer, [{HgCl2(Y)}4]n, in which the mercury(II) atom is five-coordinated and ligand Y displays C-coordination as well as an additional interaction, including O-coordination to different mercury centers and (ii) an asymmetric halide-bridged binuclear structure of the type [HgBr2(Y)]2, in which the mercury(II) center is four-coordinate and ligand Y displays C-coordination to the metal. The characterization of these compounds by IR, 1H- and 13C NMR spectroscopy confirms the coordination of the ylide to the metal through the carbon atom. Analytical data indicate a 1:1 stoichiometry between the ylide and the Hg(II) halide in all complexes.

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DOI: 10.1016/j.crci.2014.03.016
Mots-clés : Sulfonium ylide, Mercury(II) halide, Hg(II) polymer, X-ray crystal structure

Seyyed Javad Sabounchei 1; Fateme Akhlaghi Bagherjeri 1; Marjan Hosseinzadeh 1; Colette Boskovic 2; Robert W. Gable 2

1 Faculty of Chemistry, Bu-Ali Sina University, Hamedan 65174, Iran
2 School of Chemistry, University of Melbourne, Victoria 3010, Australia
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     author = {Seyyed Javad Sabounchei and Fateme Akhlaghi Bagherjeri and Marjan Hosseinzadeh and Colette Boskovic and Robert W. Gable},
     title = {X-ray crystal structure and spectral characterization of pseudo five-coordinate {Hg(II)} polymeric and four-coordinate binuclear complexes of an ambidentate sulfonium ylide},
     journal = {Comptes Rendus. Chimie},
     pages = {1257--1263},
     publisher = {Elsevier},
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     doi = {10.1016/j.crci.2014.03.016},
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Seyyed Javad Sabounchei; Fateme Akhlaghi Bagherjeri; Marjan Hosseinzadeh; Colette Boskovic; Robert W. Gable. X-ray crystal structure and spectral characterization of pseudo five-coordinate Hg(II) polymeric and four-coordinate binuclear complexes of an ambidentate sulfonium ylide. Comptes Rendus. Chimie, Volume 17 (2014) no. 12, pp. 1257-1263. doi : 10.1016/j.crci.2014.03.016. https://comptes-rendus.academie-sciences.fr/chimie/articles/10.1016/j.crci.2014.03.016/

Version originale du texte intégral

1 Introduction

Sulfur ylides R2S = C (R′) (R′′) (R, R′, R′′ = alkyl or aryl groups) are very reactive species with interesting applications in organic synthesis [1–4]. The juxtaposition of the keto group and carbanion in the α-keto stabilized sulfonium ylides permits a resonance delocalization of the ylidic electron density, providing additional stabilization to the ylide species. This allows the potential to act as an ambidentate ligand and thus to bond to a metal center through the carbanion (b) or the enolate oxygen (c). The enolate form (c) may assume either a cis or trans arrangement, the geometry of which will be retained upon bonding