Macrocyclic double ferrocenes, their stereostructure, and an IR and NMR spectroscopic, x-ray crystallographic, and conformational and dynamic investigation

Pál Sohár, Antal Csámpai, Árvácska Abrán, György Túrós, Elemér Vass, Veronika Kudar, Kálmán Újszászy, Balázs Fábián

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3 Citations (Scopus)

Abstract

Condensation reactions of 1.1'-diacetylferrocenes with hydrazine afford a series of novel ferrocenophanes with two incorporated ferrocene units. NMR spectroscopy is used to establish the free rotation of the -CH=N-N=C(R)- bridging chains (R = H, Me, Ph) and the rigidity of the -C(Me)=N-N=C(Me)- chain(s) in these macrocycles. The results of theoretical studies on molecular dynamics of these molecules cartied out by density functional calculations are consistent with the spectroscopic observations. The stereostructures of the new compounds were confirmed by IR, 1H and 13C NMR spectroscopy, including 2D-COSY, 2D-HMQC and 2D-HMBC measurements, and by mass spectrometry.

Original languageEnglish
Pages (from-to)1659-1664
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number8
DOIs
Publication statusPublished - Apr 15 2005

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Keywords

  • Density functional calculations
  • Ferrocene
  • Ferrocenophane
  • Molecular dynamics
  • Structure determination

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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