C        2-Symmetric ligands containing hydrogen bond donors: synthesis and properties of Cu(II) complexes of 2,6-bis[N,N′-(2-carboxamidophenyl)carbamoyl]pyridine

Zahida Shirin; Joel Thompson; Louise Liable-Sands; Glenn P. A. Yap; Arnold L. Rheingold; A. S. Borovik

doi:10.1039/B107166C

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C₂-Symmetric ligands containing hydrogen bond donors: synthesis and properties of Cu(ii) complexes of 2,6-bis[N,N′-(2-carboxamidophenyl)carbamoyl]pyridine

Zahida Shirin,^a Joel Thompson,^a Louise Liable-Sands,^b Glenn P. A. Yap,^b Arnold L. Rheingold^b and A. S. Borovik*^a

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* Corresponding authors

^a Department of Chemistry, University of Kansas, Lawrence, Kansas, USA

^b Department of Chemistry, University of Delaware, Newark, Delaware, USA

Abstract

The synthesis of the new tridentate ligands 2,6-bis[N,N′-(2-acetamidophenyl)carbamoyl]pyridine (H₄1^Me) and 2,6-bis[N,N′-(2-ferrocenylamidophenyl)carbamoyl]pyridine (H₄1^Fc), and their corresponding Cu^II complexes is described. In the crystalline phase, H₄1^Fc has a helical structure, which is maintained by a network of intramolecular hydrogen bonds. X-Ray diffraction studies on [CuH₂1^Me(OAc)·Cl]²⁻, [CuH₂1^Me(Cl)·Cl]²⁻, and [CuH₂1^Fc(OAc)·Cl]²⁻ reveal that the [H₂1^R]²⁻ ligands bind meridionally. One additional ligand (either OAc⁻ or Cl⁻) binds trans to the pyridyl nitrogen to complete coordination in the equatorial plane. The remaining chloride ion (Cl(1)) binds to a second sphere-binding site, which is formed by two convergent hydrogen bonding amide groups. Long Cu⋯Cl(1) bonds distances of >2.75 Å are observed. Electrochemical measurements show a 65 mV cathodic shift in the half-wave potential for [CuH₂1^Fc(OAc)·Cl]²⁻ compared to the free ligand H₄1^Fc.

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Crystal structure data TXT (104K)

Article information

DOI: https://doi.org/10.1039/B107166C
Article type: Paper
Submitted: 07 Aug 2001
Accepted: 25 Feb 2002
First published: 21 Mar 2002

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J. Chem. Soc., Dalton Trans., 2002, 1714-1720

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C ₂-Symmetric ligands containing hydrogen bond donors: synthesis and properties of Cu(II) complexes of 2,6-bis[N,N′-(2-carboxamidophenyl)carbamoyl]pyridine

Z. Shirin, J. Thompson, L. Liable-Sands, G. P. A. Yap, A. L. Rheingold and A. S. Borovik, J. Chem. Soc., Dalton Trans., 2002, 1714 DOI: 10.1039/B107166C

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Journal of the Chemical Society, Dalton Transactions