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Quantum chemical prediction of the 13C NMR shifts in alkyl and chlorocorannulenes: correction of chlorine effects

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Abstract

Prediction of the 13C NMR shifts of sym-pentachlorocorannulene and decachlorocorannulene provided impetus for the development of a correction scheme based on a regression of experimental and quantum chemical data. A training set of 15 compounds (18 carbon signals) comprising carbons atoms bearing 1–4 chlorine atoms leads to an estimated error per chlorine atom of about 10–12 ppm. Specifically, linear regression of the data obtained at B3LYP/cc-pVDZ leads to y = −3.77 + 13.11x, with R = 0.982. Ultimately, experiment and theory converge for sym-pentachlorocorannulene and decachlorocorannulene, the former by correction of the theory, the latter by collecting the proper experimental data.

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Authors and Affiliations

  1. Organic Chemistry Institute, University of Zurich, 190 Winterthurerstrasse, 8057, Zurich, Switzerland

    Kim K. Baldridge & Jay S. Siegel

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  1. Kim K. Baldridge
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  2. Jay S. Siegel
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Correspondence to Kim K. Baldridge.

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Contribution to the Mark S. Gordon 65th Birthday Festschrift Issue.

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Baldridge, K.K., Siegel, J.S. Quantum chemical prediction of the 13C NMR shifts in alkyl and chlorocorannulenes: correction of chlorine effects. Theor Chem Account 120, 95–106 (2008). https://doi.org/10.1007/s00214-007-0291-9

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