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Aminoferrocene is an electron rich molecule with a metallocene backbone. It is a useful precursor for peptide bioconjugate and prodrug synthesis, as an electroactive indicator, in biosensors and as a fuel cell catalyst. It also has a number of biological applications as an antiparasitic and anticancer drug and a donor in photosynthesis.
Aminoferrocene possesses high chemical stability, low boiling point, and solubility in less polar organic solvents. This makes it an important raw material for the synthesis of organic molecules, catalysts and ferromolecular materials. It has a variety of technological and medical applications as well, including the production of polyethylene, plastic and rubber and its use as a heat transfer agent and lubricant.
It has a large variety of industrial uses in the synthesis of polymers, as a catalyst and in the synthesis of metal complexes. Aminoferrocene is also used as a ligand in a wide range of organic reactions and in the synthesis of pharmaceuticals.
A recent discovery of the structural features of aminoferrocene 1 reveals that it has a unique sandwich structure involving an iron center and two cyclopentadienyl rings. The isoenergetic eclipsed and staggered conformations of the cyclopentadienyl ring(Cp) have been established by X-ray crystallography and nuclear magnetic resonance (NMR).
Single crystal X-ray diffraction confirmed the existence of an intrachain N-H***O hydrogen bond between the NH group bound to one Cp ring and the carboxylate moiety bound to another one. This bond stabilises the conformation of Boc-Pro-Fca-OMe (3), while its interchain dipolar interaction with other atoms in the molecule contributes to its overall stability.