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Updated: Nov 14, 2025

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
Published on: March 12, 2015
Estimating Effective Steric and Electronic Impacts of a Ferrocenyl Group in Organophosphines
Hao Hu1,2, Hiroki Ichiryu1, Kiyohiko Nakajima3
1Department of Natural Science, Graduate School of Science and Technology, Tokushima International Science Institute, and Research Cluster on ″Innovative Chemical Sensing″, Tokushima University, Tokushima 770-8506, Japan.
Abstract:
A series of monodentate ferrocenylphosphines, Fc3P (1a), Fc2PhP (1b), and Fc2ArP (1c; Fc = ferrocenyl, Ar = 3,4-methylenedioxyphenyl), were prepared, and their electronic and steric properties were quantitatively determined. By the IR measurements of their respective Ni(CO)3(phosphine) complexes, the electronic properties of the ferrocenyl group in organophosphines were estimated to be similar to those of primary alkyl groups. The ferrocenyl group is a better electron donor than a methyl group and a poorer donor than an ethyl group. The gold(I) chloride complexes of 1a-c were prepared and their X-ray crystal structures were determined. The %V bur parameters for 1a-c were calculated using the X-ray structural data, and their ″Tolman cone angles″ were estimated. The steric influence of the ferrocenyl group in organophosphines was clarified to be larger than those of cyclohexyl, tert-butyl, and o-tolyl groups and is comparable to that of a mesityl group.
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