Elucidating the Relative and Absolute Configuration of Organic Compounds by Quantum Mechanical Approaches
Gianluigi Lauro, Giuseppe Bifulco
Abstract
Different examples of the application of quantum mechanical (QM) methods combined with experimental approaches, such as NMR spectroscopy and electronic circular dichroism (ECD), are reported to highlight their successful application in the determination of the stereochemical arrangement of organic compounds. A first part is dedicated to various examples and methodological studies based on the comparison of experimental NMR parameters ( 13 C and 1 H NMR chemical shifts, homonuclear and heteronuclear J coupling constants) and their related values calculated at the QM theory level, with particular applications in the assignment of the relative configuration of organic compounds. A final section is focused on the determination of the absolute configuration by the comparison of experimental and predicted NMR parameters and ECD spectra.