Premium
Elucidating the Relative and Absolute Configuration of Organic Compounds by Quantum Mechanical Approaches
Author(s) -
Lauro Gianluigi,
Bifulco Giuseppe
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901878
Subject(s) - homonuclear molecule , heteronuclear molecule , chemistry , absolute configuration , coupling constant , circular dichroism , computational chemistry , nuclear magnetic resonance spectroscopy , chemical shift , spectroscopy , carbon 13 nmr satellite , fluorine 19 nmr , stereochemistry , molecule , organic chemistry , quantum mechanics , physics
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.