Binding of nitrate to a CuII-cyclen complex bearing a ferrocenyl pendant: synthesis, solid-state X-ray structure, and solution-phase electrochemical and spectrophotometric studies

Inorg Chem. 2007 May 14;46(10):3876-88. doi: 10.1021/ic061622+. Epub 2007 Apr 17.

Abstract

The reaction of Cu(NO3)2.3H2O with the ligand 1-(ferrocenemethyl)-1,4,7,10-tetraazacyclododecane (L) in acetonitrile leads to the formation of a blue complex, [Cu(L)(NO3)][NO3] (C1). The X-ray structure determination shows an unexpected binding of a nitrate anion in that the CuII center is surrounded by four N atoms of the 1,4,7,10-tetraazacyclododecane (cyclen) macrocycle and two O atoms from a chelating nitrate anion, both Cu-O distances being below the sums of the van de Waals radii. Hydrogen-bonding interactions in the crystal lattice and a weak interaction between a second nitrate O and the CuII center in C1 give rise to a highly distorted CuII geometry relative to that found in the known structure of [Cu(cyclen)(NO3)][NO3] (C5). Electrochemical studies in acetonitrile containing 0.1 M [Bu4N][NO3] as the supporting electrolyte showed that oxidation of C1 in this medium exhibits a single reversible one-electron step with a formal potential E degrees f of +85 mV vs Fc0/+ (Fc = ferrocene). This process is associated with oxidation of the ferrocenyl pendant group. Additionally, a reversible one-electron reduction reaction with an E degrees f value of -932 mV vs Fc0/+, attributed to the CuII/I redox couple, is detected. Gradual change of the supporting electrolyte from 0.1 M [Bu4N][NO3] to the poorly coordinating [Bu4N][PF6] electrolyte, at constant ionic strength, led to a positive potential shift in E degrees f values by +107 and +39 mV for the CuII/I(C1) and Fc0/+(C1) redox couples, respectively. Analysis of these electrochemical data and UV-vis spectra is consistent with the probable presence of the complexes C1, [Cu(L)(CH3CN)2]2+ (C2), [Cu(L)(CH3CN)(NO3)]+ (C3), and [Cu(L)(NO3)2] (C4) as the major species in nitrate-containing acetonitrile solutions. In weakly solvating nitromethane, the extent of nitrate complexation remains significant even at low nitrate concentrations, due to the lack of solvent competition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chelating Agents / chemistry*
  • Copper / chemistry*
  • Crystallography, X-Ray
  • Cyclams
  • Electrochemistry
  • Ferrous Compounds / chemistry*
  • Heterocyclic Compounds / chemistry*
  • Hydrogen Bonding
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Nitrates / chemistry*
  • Spectrophotometry, Ultraviolet

Substances

  • Chelating Agents
  • Cyclams
  • Ferrous Compounds
  • Heterocyclic Compounds
  • Indicators and Reagents
  • Nitrates
  • Copper
  • cyclen