Enantiomeric recognition of chiral invertomers through NMR in chiral oriented phases: a study of cis-decalin |
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| Institution: | 1. Dipartimento di Scienze, Università Roma Tre, Viale G. Marconi, 446- 00146 Roma, Italy;2. Dipartimento di Fisica, Università di Roma “Tor Vergata”, Via Della Ricerca Scientifica, 1- 00133 Roma, Italy;3. Dipartimento di Scienze Fisiche e Chimiche, Università degli Studi dell''Aquila, L''Aquila, Italy;1. Swiss–Norwegian Beam Lines at European Synchrotron Radiation Facility, CS 40220, 38043 Grenoble Cedex 9, France;2. Southern Federal University, 5 Zorge St., 344090 Rostov-on-Don, Russia;3. Southern Scientific Center of the Russian Academy of Science, 41 Chekhova Ave., 344006 Rostov-on-Don, Russia;4. Peter the Great St. Petersburg Polytechnic University, 29, Polytechnicheskaya St., 195251 St. Petersburg, Russia;5. Institute of Crystallography R.A.S., Leninsky pr. 59, 119333 Moscow, Russia;1. Department of Physics and Astronomy, Wayne State University, Detroit, MI 48201, USA;2. Chemistry Division, Bhabha Atomic Research Centre, Mumbai 400085, India;3. Department of Natural Sciences, University of Michigan, Dearborn, MI 48128, USA |
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| Abstract: | We describe a deuterium 1D and 2D NMR study of cis-decalin in various chiral and achiral polypeptide oriented solvent systems and the effect of the acquisition temperature. Organic solutions of poly-γ-benzyl-l-glutamate (PBLG) or poly-ε-carbobenzyloxy-l-lysine (PCBLL) in dichloromethane or chloroform allow the chiral invertomers of cis-decalin to be differentiated at low temperature. At high temperature, it is possible to distinguish between deuterium nuclei of the molecule which become enantiotopic under rapid kinetic averaging. The results obtained illustrate the capability of such polypeptide liquid-crystalline solvents to enantioselectively interact with unfunctionalised chiral cycloalkanes and highlight the analytical potential of NMR analysis in chiral liquid crystal based solvents in the investigation of interconverting chiral conformers. |
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