ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

On Ferrocene Derivatives. XIX. Relative Basicity Examination of Ferrocene Analogues of Chalcones on the Basis of Infrared Spectra

Š. Toma and A. Perjéssy

Department of Organic Chemistry, Faculty of Natural Sciences, Komenský University, Bratislava 1

Abstract: The formation of a H bond between PhOH and ferrocene analogs of chalcones was investigated on the basis of stretching vibration shift of the phenolic OH group. Shifts Δν(OH) of chclcones of general formula FeCOCH:CHAr (type A) or those of general formula FeCH:CHCOAr (type B), where Fe = ferrocenyl, can be well correlated with σ⁺ consts. Shifts of chalcones PhCOC₅H₄FeC₅H₄COCH:CHAr (type C) are correlated either with σ or σ⁺ consts. σ and σ⁺ consts. were calcd. for ferrocenyl(Fc),2-thienyl, and 2-furyl. The relative basicity of chalcones decreased in the order: ferrocenyl » 2-furyl > 2-thienyl > Ph in all cases.

Full paper in Portable Document Format: 235a343.pdf

Chemical Papers 23 (5) 343–351 (1969)