Journal article

Publication year: 2015

Pages: 6520-6524

Journal: The Journal of Organic Chemistry

Volume number: 80

Issue number: 12

ISSN: 0022-3263

DOI Link: https://doi.org/10.1021/acs.joc.5b00845

Publisher: American Chemical Society

Abstract: 

Disproving a long C–C-bond textbook example: The reported 1.643 Å C–C
bond in 5-cyano-1,3-dehydroadamantane was redetermined and “only”
amounts to 1.584 Å. While this value is well reproduced with ab initio
methods, some common DFT approaches perform poorly and are only
consistent with CCSD(T)/cc-pVTZ optimizations for noninverted carbons.
Large deviations from experiment were also found for other molecules
with atypical electron density distributions, e.g., cubane,
bicyclo[2.2.0]hexane, and bicyclo[2.1.0]- and bicyclo[1.1.1]pentane,
thereby presenting challenging structures for some DFT implementations.

Harvard Citation style: Bremer, M., Untenecker, H., Gunchenko, P., Fokin, A. and Schreiner, P. (2015) Inverted Carbon Geometries: Challenges to Experiment and Theory, The Journal of Organic Chemistry, 80(12), pp. 6520-6524. https://doi.org/10.1021/acs.joc.5b00845

APA Citation style: Bremer, M., Untenecker, H., Gunchenko, P., Fokin, A., & Schreiner, P. (2015). Inverted Carbon Geometries: Challenges to Experiment and Theory. The Journal of Organic Chemistry. 80(12), 6520-6524. https://doi.org/10.1021/acs.joc.5b00845