Structural, spectroscopic and theoretical studies of the 2:2 complex of 5,5′-dibromo-2,2′-biphenol with 1,5,7-triazabicyclo[4.4.0]dec-5-ene

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

Research output: Contribution to journalArticle

Abstract

In the crystal of the 2:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene with 5,5′-dibromo-2,2′-biphenol a cooperative inter-intra-molecular hydrogen-bonded system is formed. The intermolecular hydrogen bonds are relatively long [2.708(6) and 2.895(7)] and do not show large proton polarizability. The intramolecular OHO- hydrogen bond is relatively short [2.489(6)]. The structure of the complex is very well reflected in its FT-IR spectrum in the solid. On the basis of the FT-IR and 1H NMR studies of the complex in chloroform and in acetonitrile a structure different than in the solid is proposed. DFT structures of both isolated ions in their ground electronic states at the B3LYP/6-31 + +G(d,p) level are employed to follow the effects of the hydrogen bonding on the intrinsic ionic structures.

Original languageEnglish (US)
Pages (from-to)153-159
Number of pages7
JournalJournal of Molecular Structure
Volume598
Issue number2-3
DOIs
StatePublished - Jan 1 2001

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Keywords

  • 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)
  • 5,5′-Dibromo-2,2′-biphenol
  • Ab initio calculations
  • Crystal structure
  • FT-IR spectroscopy
  • H NMR spectroscopy
  • Hydrogen bond
  • Strong N-base

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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