Cooperative intramolecularly hydrogen-bonded motif in the structure of 2:2 complex of TBD with 4-nitrocatechol

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

Research output: Contribution to journalArticlepeer-review


In the crystal of the 2:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene with 4-nitrocatechol the proton from 1-hydroxyl group of 4-nitrocatechol moiety is transferred to TBD to form ion-pair; two adjacent ion-pairs are linked across a center of inversion. The structure exhibits a cooperative, intramolecularly hydrogen-bonded motif. The hydrogen bonds are relatively long and, and they display only minor proton polarizability. The structure of the complex is retained in chloroform solution, as shown by FT-IR and 1H NMR measurement; in acetonitrile, the compound partially dissociates. The partial dissociation is implied by the presence of free cations, and also by that of the (O···H···O)- hydrogen bonds formed between two monodeprotonated 4-nitrocatechol molecules.

Original languageEnglish (US)
Pages (from-to)139-145
Number of pages7
JournalJournal of Molecular Structure
Issue number1-3
StatePublished - Jul 19 2001


  • 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
  • Cooperative hydrogen bonds
  • Crystal structure
  • FT-IR spectroscopy
  • H NMR spectroscopy
  • Intramolecular hydrogen bonds
  • Strong N-base

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry


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