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, Pance Naumov, M. G.B. Drew, G. Wojciechowski, B. Brzezinski

Research output: Contribution to journalArticle

Abstract

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
Volume595
Issue number1-3
DOIs
StatePublished - Jan 1 2001

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Anions
Ions
Dimers
Protons
Hydrogen
Nitrogen
Infrared radiation
Atoms
Acids
Geometry
dicyclohexylamine
3,5-dinitrosalicylic acid

Keywords

  • 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

Cite this

Structural and spectroscopic studies on 3,5-dinitrosalicylic acid complexes of urotropine and dicyclohexylamine. A theoretical analysis of the structure of the complex anion. / Ng, S. W.; Naumov, Pance; Drew, M. G.B.; Wojciechowski, G.; Brzezinski, B.

In: Journal of Molecular Structure, Vol. 595, No. 1-3, 01.01.2001, p. 29-37.

Research output: Contribution to journalArticle

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AU - Ng, S. W.

AU - Naumov, Pance

AU - Drew, M. G.B.

AU - Wojciechowski, G.

AU - Brzezinski, B.

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AB - 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.

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KW - Proton polarizability

KW - Theoretical calculations

KW - Urotropine

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