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WIREs Comput Mol Sci
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Addressing the stereochemistry of complex organic molecules by density functional theory‐ NMR

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Determining the stereochemistry of organic molecules is a long‐standing problem, with implications for stereoselective reactions, catalysis, and the structure of natural products. NMR spectroscopy is widely employed to this purpose; however, the interpretation of results is often entrusted to empirical methods or expert systems. Quantum chemical calculations, generally based on density functional theory, provide a reliable framework to predict the relevant parameters (chemical shifts and coupling constants, generally involving 1H and 13C) of diastereoisomers with useful accuracy. While the approach virtually spans all molecules of interest in organic chemistry, including those that contain heavy atoms, the analysis of results still poses significant challenges. WIREs Comput Mol Sci 2015, 5:228–240. doi: 10.1002/wcms.1214

Calculated versus experimental 1H shifts of strychnine (Ref ). Statistical parameters: R2 = 0.9977; MAE = 0.12 ppm; CMAE = 0.07 ppm. See text for definitions.
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Reprinted adapted with permission from Ref . Copyright 2010 American Chemical Society.
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Reprinted adapted with permission from Ref . Copyright 2011 American Chemical Society.
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Correlation coefficients obtained by the linear regression δcalc = a + bδexp using the calculated δ(13C) values for the eight isomers of Scheme : (filled squares) the experimental δ(13C) data of vannusal B; (empty circles) the experimental δ(13C) values of the vannusals of Scheme .
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Reprinted adapted with permission from Ref . Copyright 2011 American Chemical Society.
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Structure and Mechanism > Reaction Mechanisms and Catalysis
Theoretical and Physical Chemistry > Spectroscopy
Electronic Structure Theory > Density Functional Theory

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