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Vibrational CD study on the solution phase structures of the MacMillan catalyst and its corresponding iminium ion.

Tino P GolubChristian Merten
Published in: Physical chemistry chemical physics : PCCP (2021)
We demonstrate that VCD spectroscopy can reveal insights into the conformational preferences of the iminium ion obtained from MacMillan's imidazolidinone catalyst. For both the isolated and in situ generated iminium ion, the comparison of experimental and computed VCD spectra directly confirms that conformer 2b ("Houk-conformer") is the dominant structure in solution. This conclusion is reached without any in-depth interpretation of the spectroscopic data, just by visual comparison of the spectral signatures. For the parent catalyst 1 and its salts 1·HCl and 1·HClO4, we report a comprehensive analysis of the conformational preferences in two solvents. VCD spectroscopy is subsequently shown to be able to reveal small conformational changes induced by solute-solvent and solute-anion interactions.
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