Structural and spectroscopic studies on 3,5-dinitrosalicylic acid complexes of urotropine and dicyclohexylamine. A theoretical analysis of the structure of the complex anion

S. W. Ng, P. Naumov, M. G.B. Drew, G. Wojciechowski, B. Brzezinski

Research output: Contribution to journalArticle


In the reaction between 3,5-dinitrosalicylic acid and urotropine, the proton of the phenolic group is transferred to a nitrogen atom of urotropine to form a hydrogen-bonded ion-paired [N⋯Ophenolate = 2.777(4) A˚] compound. An analogous reaction between the acid and dicyclohexylamine yields a centrosymmetric ion-paired dimer [N⋯Ophenolate = 2.864(4), N⋯Ocarbonyl = 2.940(5) A˚]. The structures of the two compounds are discussed in relation to their infrared spectral features. The structure of the anion is also investigated theoretically by geometry-optimization calculations.

Original languageEnglish (US)
Pages (from-to)29-37
Number of pages9
JournalJournal of Molecular Structure
Issue number1-3
StatePublished - Sep 12 2001



  • 3,5-Dinitrosalicylic acid
  • Crystal structure
  • Dicyclohexylamine
  • FT-IR spectroscopy
  • Hydrogen bonds
  • NMR spectroscopy
  • Proton polarizability
  • Theoretical calculations
  • Urotropine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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