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Issue 18, 2019
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Ferrocenes with simple chiral substituents: an in-depth theoretical and experimental VCD and ECD study

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Abstract

Circular dichroism spectra in the IR range (VCD = vibrational circular dichroism) and in the UV range (ECD = electronic circular dichroism) have been recorded for both enantiomers of simple mono-substituted ferrocenes containing chiral pendants: 1-acetoxyethylferrocene, 1, 1-methoxyethylferrocene, 2, and 1-hydroxyethylferrocene, 3; the related disubstituted 1,1′-bis(1-hydroxyethyl)ferrocene, 4, was also considered. These two types of spectra, with the support of DFT calculations, concur to unequivocally confirm the absolute configuration for 1–4. In particular, our computational results point out the clear advantage of using an anharmonic oscillator model for the interpretation of VCD spectra of chiral ferrocenes. Interesting conformational properties are either confirmed or established by the technique, like the eclipsed conformation of the two cyclopentadienyl rings and an intra-molecular interaction involving the OH for 3. For 4, NMR, VCD and IR spectra are compatible with dimer formation and in this case a distorted conformation is predicted. Of utmost importance for the absolute configuration assignment in mono-substituted ferrocenes, we were able to identify a diagnostic VCD band at 950 cm−1 and a (low intensity) ECD band that clearly indicate the absolute configuration of the whole series.

Graphical abstract: Ferrocenes with simple chiral substituents: an in-depth theoretical and experimental VCD and ECD study

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Supplementary files

Article information


Submitted
23 Jan 2019
Accepted
09 Apr 2019
First published
10 Apr 2019

Phys. Chem. Chem. Phys., 2019,21, 9419-9432
Article type
Paper

Ferrocenes with simple chiral substituents: an in-depth theoretical and experimental VCD and ECD study

A. Patti, S. Pedotti, G. Mazzeo, G. Longhi, S. Abbate, L. Paoloni, J. Bloino, S. Rampino and V. Barone, Phys. Chem. Chem. Phys., 2019, 21, 9419
DOI: 10.1039/C9CP00437H

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