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Synthesis and spectroscopic studies on charge–transfer molecular complexes formed in the reaction of imidazole and 1-benzylimidazole with σ- and π-acceptors

Authors
Journal
Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy
1386-1425
Publisher
Elsevier
Publication Date
Volume
79
Issue
5
Identifiers
DOI: 10.1016/j.saa.2011.05.021
Keywords
  • Imidazole
  • 1-Benzylimidazole
  • Iodine
  • Ddq
  • Tcne
  • Chl
Disciplines
  • Physics

Abstract

Abstract The spectrophotometric characteristics of the solid charge–transfer molecular complexes (CT) formed in the reaction of the electron donors imidazole (IML) and 1-benzylimidazole (BIML) with the σ-acceptor iodine and π-acceptors 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), tetracyanoethylene (TCNE) and 2,3,5,6-tetrachloro-1,4-benzoquinone (CHL) have been studied in chloroform at 25 °C. These were investigated through electronic and infrared spectra as well as elemental analysis. The results show that the formed solid CT-complexes have the formulas [(IML) 2 I]I 3, [(IML)(DDQ)], [(IML) 2(TCNE) 5] and [(IML)(CHL)] for imidazole and [(BIML) I]I 3, [(BIML)(DDQ) 2], [(BIML)(TCNE) 2] and [(BIML)(CHL) 2] for 1-benzylimidazole in full agreement with the known reaction stoichiometries in solution as well as the elemental measurements. The formation constant K CT, molar extinction coefficient ɛ CT, free energy change Δ G 0, CT energy E CT and ionization potential Ip have been calculated for the CT-complexes [(IML) 2 I]I 3, [(IML)(DDQ)], [(IML)(CHL)], [(BIML) I]I 3, [(BIML)(DDQ) 2], [(BIML)(TCNE) 2] and [(BIML)(CHL) 2].

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