Issue 20, 2002
From the journal:

Journal of the Chemical Society, Dalton Transactions

1,2-Bis(2-benzimidazolyl)-1,2-ethanediol, a chiral, tridentate, facially coordinating ligand

Katharina Isele,a   Vanessa Broughton,a   Craig J. Matthews,a   Alan F. Williams,*a   Gérald Bernardinelli,b   Patrick Franzc  and  Silvio Decurtinsc  

* Corresponding authors

a Département de Chimie Minérale, Analytique et Appliquée, Université de Genève, 30 quai Ernest Ansermet, CH 1211 Genève 4, Switzerland

b Laboratoire de Cristallographie aux Rayons-X, Université de Genève, 24 quai Ernest Ansermet, CH 1211 Genève 4

c Institut für Chemie und Biochemie, Universität Bern, Freiestrasse 3, CH 3012 Bern, Switzerland

Abstract

The ligand 1,2-bis(1H-benzimidazol-2-yl)-1,2-ethanediol, 1, and its methylated derivative 2 are readily synthesized from tartaric acid, and act as chiral, facially coordinating tridentate ligands, forming complexes of composition ML2 with octahedral transition metals. The copper(II) complexes show distorted 4 + 2 coordination with benzimidazoles occupying the equatorial sites and alcohol functions weakly binding in the axial sites. Nickel(II) complexes in three different states of protonation show regular octahedral geometry with the alcohols mutually cis. Deprotonation of the coordinated alcohol produces little structural change but the monodeprotonated complex forms a hydrogen bonded dimer. Magnetic measurements show the hydrogen bonded bridge to offer a pathway for weak antiferromagnetic coupling. UV-Visible spectroscopy shows the ligand to have a field intermediate between water and pyridine. The diastereoselectivity of complexation depends on the geometry: nickel(II) shows a weak preference for the homochiral complex, whereas copper(II) forms almost exclusively homochiral complexes.

Graphical abstract: 1,2-Bis(2-benzimidazolyl)-1,2-ethanediol, a chiral, tridentate, facially coordinating ligand

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Article information

DOI
https://doi.org/10.1039/B203229E
Article type
Paper
Submitted
03 Apr 2002
Accepted
01 Aug 2002
First published
16 Sep 2002

J. Chem. Soc., Dalton Trans., 2002, 3899-3905

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1,2-Bis(2-benzimidazolyl)-1,2-ethanediol, a chiral, tridentate, facially coordinating ligand

K. Isele, V. Broughton, C. J. Matthews, A. F. Williams, G. Bernardinelli, P. Franz and S. Decurtins, J. Chem. Soc., Dalton Trans., 2002, 3899 DOI: 10.1039/B203229E

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