Structure elucidation and DFT-study on substrate-selective formation of chalcones containing ferrocene and phenothiazine units. Study on ferrocenes, Part 17

Tamás Lovász, György Túrós, Luiza Gǎinǎ, A. Csámpai, Dávid Frigyes, Balázs Fábián, Ioan A. Silberg, P. Sohár

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

By means of base-catalysed condensation of 1-acyl-/1,1′- diacylferrocenes (acylformyl or acetyl) with 3-formyl- and 3,7- diacetylphenothiazines a series of novel mono- and bis-chalcones were prepared. The enhanced reactivity of the enolate anions of the mono-chalcone intermediates relative to that of the enolates of the corresponding diacetyl-substituted precursor was interpreted by the electron-releasing effect of the ferrocenyl- or phenothiazinyl group present in the β position of the enone subunit. The structures of the novel products were evidenced by IR, 1H and 13C NMR spectroscopy including 2D-COSY, 2D-HSQC and 2D-HMBC measurements.

Original languageEnglish
Pages (from-to)100-108
Number of pages9
JournalJournal of Molecular Structure
Volume751
Issue number1-3
DOIs
Publication statusPublished - Sep 15 2005

Fingerprint

Chalcones
ferrocenes
phenothiazines
releasing
Discrete Fourier transforms
Nuclear magnetic resonance spectroscopy
Condensation
Negative ions
reactivity
condensation
anions
Chalcone
Diacetyl
nuclear magnetic resonance
Electrons
Substrates
products
spectroscopy
Anions
electrons

Keywords

  • DFT calculations
  • Ferrocene
  • Nucleophilicity
  • Phenothiazine
  • Structure elucidation by IR and NMR

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics
  • Materials Science (miscellaneous)

Cite this

Structure elucidation and DFT-study on substrate-selective formation of chalcones containing ferrocene and phenothiazine units. Study on ferrocenes, Part 17. / Lovász, Tamás; Túrós, György; Gǎinǎ, Luiza; Csámpai, A.; Frigyes, Dávid; Fábián, Balázs; Silberg, Ioan A.; Sohár, P.

In: Journal of Molecular Structure, Vol. 751, No. 1-3, 15.09.2005, p. 100-108.

Research output: Contribution to journalArticle

Lovász, Tamás ; Túrós, György ; Gǎinǎ, Luiza ; Csámpai, A. ; Frigyes, Dávid ; Fábián, Balázs ; Silberg, Ioan A. ; Sohár, P. / Structure elucidation and DFT-study on substrate-selective formation of chalcones containing ferrocene and phenothiazine units. Study on ferrocenes, Part 17. In: Journal of Molecular Structure. 2005 ; Vol. 751, No. 1-3. pp. 100-108.
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AU - Gǎinǎ, Luiza

AU - Csámpai, A.

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