Structural, theoretical and spectroscopic studies of the 1:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene-4-nitrophenol

S. W. Ng, P. Naumov, S. Chantrapromma, S. Shanmuga Sundara Raj, H. K. Fun, A. R. Ibrahim, G. Wojciechowski, B. Brzezinski

Research output: Contribution to journalArticlepeer-review


In the crystal of the 1:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene with 4-nitrophenol one hydrogen atom of the phenolic group is transferred to the TBD molecule and two NH protons form hydrogen bonds with one nitro group [N···O distances are 2.968(5), 2.985(4) Å]. This hydrogen-bonded segment is linked to another molecule of 4-nitrophenol by a short (O···H···O)- hydrogen bond [O···O = 2.512(3)Å]. The structure of the cation is investigated theoretically by geometry-optimization calculations. The structure of the complex is very well reflected in its FTIR spectrum in the solid. The complex dissolution in acetonitrile causes its dissociation and its FTIR and 1H NMR spectra prove the presence of the protonated TBD and (O···H···O)- hydrogen-bonded 4-nitrophenol-4-nitrophenolate species. In chloroform a new structure of the complex is found and discussed.

Original languageEnglish (US)
Pages (from-to)185-196
Number of pages12
JournalJournal of Molecular Structure
Issue number1-3
StatePublished - May 2 2001


  • Crystal structure
  • FTIR spectroscopy
  • Intramolecular hydrogen bond
  • NMR spectroscopy
  • Strong N-base
  • TBD
  • Theoretical calculations

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry


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