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Calculating Accurate Proton Chemical Shifts of Organic Molecules with Density Functional Methods and Modest Basis Sets

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Department of Chemistry, University of Fribourg, CH-1700 Fribourg, Switzerland, and Department of Chemistry and Biochemistry, Swarthmore College, Swarthmore, Pennsylvania 19081-1397
[email protected]; [email protected]
†University of Fribourg.
‡Current address: IIT Bombay, India.
§Swarthmore College.
Cite this: J. Org. Chem. 2009, 74, 11, 4017–4023
Publication Date (Web):May 12, 2009
https://doi.org/10.1021/jo900482q
Copyright © 2009 American Chemical Society
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Abstract

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The purpose of this paper is to convince practitioners of 1H NMR spectroscopy to consider simple quantum chemical calculations as a viable option to aid them in the assignment of their spectra. To this end, it is demonstrated, on a test set of 80 conformationally stable molecules of various kinds carrying different functional groups, that, in contrast to what is claimed in the literature, large basis sets are not needed to obtain rather accurate predictions of 1H NMR chemical shifts by quantum chemical calculations. On the other hand, modeling the solvent by an SCRF-type calculation may improve certain predictions significantly. The best accuracy/cost ratio is provided by GIAO calculations in chloroform as a solvent with the specially parametrized WP04 functional of Cramer et al. using the cc-pVDZ or 6-31G** basis set, closely followed by similar calculations with the ubiquitious B3LYP functional (both predict 1H chemical shifts with an average deviation of ca. 0.12 ppm, if the results are scaled linearly). A slightly higher accuracy can be attained by adding diffuse functions to the basis set, but going to the triple-ζ basis sets which have invariably been used hitherto in calculations of chemical shifts does not lead to any improvement. The popular increment schemes such as those implemented in the ChemDraw or ACD programs do not do nearly as well and are often incapable of correctly distinguishing stereoisomers.

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(a) Complete ref 30; (b) structures of the 80 molecules in the test set; (c) table with the complete data from the calculations with the “probe” set depicted in Figure 2; (d) Excel spreadsheets containing all the raw data and the statistical workup for the test and for the “probe” set; (e) a complete Gaussian input to run a calculation on the entire test set or probe set of molecules ((d) and (e) are packed into a zip-archive). This material is available free of charge via the Internet at http://pubs.acs.org.

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