Vibrational circular dichroism of 3‐(trifluoroacetyl)‐camphor and its interaction with chiral amines |
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| Authors: | Christian Merten Karl J Jalkanen Volker C Weiss Andreas Hartwig |
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| Institution: | 1. Fraunhofer Institute of Manufacturing Technology and Applied Materials Research (IFAM), Department of Adhesive Bonding Technology and Surfaces, 28359 Bremen, Germany;2. Bremen Center for Computational Materials Science (BCCMS), Universit?t Bremen, 28359 Bremen, Germany;3. Nanochemistry Research Institute (NRI), Curtin University of Technology, Perth, WA 6845, Australia |
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| Abstract: | Vibrational circular dichroism (VCD) spectroscopy and density functional theory (DFT) calculations are used to investigate the keto–enol equilibrium of 3‐(trifluoroacetyl)‐camphor (TFC) and to study the interaction of TFC with chiral amines in deuterated Chloroform. It is shown that the VCD spectra of the enol‐ and keto forms of TFC can clearly be distinguished and that the enol form is favored. By deprotonation of the TFC enol with chiral amines, no indication of a mutual diasteriomeric influence on the VCD spectra induced by transfer of stereochemical information between the chiral ionic species is found, neither experimentally nor theoretically. Chirality 2010. © 2010 Wiley‐Liss, Inc. |
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| Keywords: | vibrational circular dichroism density functional theory keto– enol equilibrium Coulomb interaction ion pairing |
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