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Towards unbiased and more versatile NMR‐based structure elucidation: A powerful combination of CASE algorithms and DFT calculations
Author(s) -
Buevich Alexei V.,
Elyashberg Mikhail E.
Publication year - 2018
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.4645
Subject(s) - chemistry , molecule , heteronuclear single quantum coherence spectroscopy , density functional theory , computational chemistry , chemical shift , structural isomer , small molecule , halogen , carbon 13 nmr , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , biochemistry , alkyl
Computer‐assisted structure elucidation (CASE) is composed of two steps: (a) generation of all possible structural isomers for a given molecular formula and 2D NMR data (COSY, HSQC, and HMBC) and (b) selection of the correct isomer based on empirical chemical shift predictions. This method has been very successful in solving structural problems of small organic molecules and natural products. However, CASE applications are generally limited to structural isomer problems and can sometimes be inconclusive due to insufficient accuracy of empirical shift predictions. Here, we report a synergistic combination of a CASE algorithm and density functional theory calculations that broadens the range of amenable structural problems to encompass proton‐deficient molecules, molecules with heavy elements (e.g., halogens), conformationally flexible molecules, and configurational isomers.