A conformational analysis of the spirocyclic quaternary ammonium cation [(CH2)4N(CH2)4]+ in its bromide and picrate salts

Uwe Monkowius, Stefan Nogai, Hubert Schmidbaur

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

High-yield syntheses of the bromide (1a) and picrate salts (1b) of the 5-azonia-spiro[4]nonane cation [(CH2)4N(CH 2)4]+ are reported. In the single crystal X-ray diffraction analyses of the two salts the spirocyclic quaternary ammonium cations have their five-membered rings in envelop and twist conformations modified by packing forces. The conformation found experimentally for 1a has C2 -symmetry as predicted for the gas phase by quantum-chemical calculations (RI-DFT, RI-MP2), but the five-membered rings are intermediate between the expected envelop and the twist form. For 1b, both of the two independent cations can be described as a combination of rings in an envelop and a twist conformation. According to the NMR spectra, in solution the cations are highly flexible and pseudosymmetrical (point group D2d).

Original languageEnglish
Pages (from-to)259-263
Number of pages5
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume59
Issue number3
DOIs
StatePublished - Mar 2004
Externally publishedYes

Keywords

  • 5-Azoniaspirononane Cation
  • Conformational Analysis
  • Heterospirononanes
  • Spirocyclic Ammonium Salts

Fingerprint

Dive into the research topics of 'A conformational analysis of the spirocyclic quaternary ammonium cation [(CH2)4N(CH2)4]+ in its bromide and picrate salts'. Together they form a unique fingerprint.

Cite this