Universität zu Köln

Zhang, Jun and Dolg, Michael ORCID: 0000-0002-0538-0837 (2014). Dispersion Interaction Stabilizes Sterically Hindered Double Fullerenes. Chem.-Eur. J., 20 (43). S. 13909 - 13913. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3765

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Abstract

By state-of-the-art quantum chemical methods, we show that for bulky functional groups like cyclohexane, [20]fullerene, dodecahedrane, and C-60, the attractive dispersion interaction can have a greater impact on stereochemistry than the repulsive steric effect, making the compact isomer the more stable one. In particular, for the double C-60 adduct of pentacene 1, the syn isomer should be the main product instead of the anti one inferred in the original synthesis experiment (Y. Murata et al., J. Org. Chem. 1999, 64, 3483). With and without dispersion interactions taken into account, the Gibbs energy difference Delta G(syn-anti) is -6.36 and +1.15 kcal mol(-1), respectively. This study reminds us that dispersion interactions as well as electrostatic or hyperconjugation effects, etc. can lead to some unusual stereochemical phenomena.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Zhang, Jun UNSPECIFIED UNSPECIFIED UNSPECIFIED Dolg, Michael UNSPECIFIED orcid.org/0000-0002-0538-0837 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-425634
DOI:	10.1002/chem.201404106
Journal or Publication Title:	Chem.-Eur. J.
Volume:	20
Number:	43
Page Range:	S. 13909 - 13913
Date:	2014
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3765
Language:	English
Faculty:	Faculty of Management, Economy and Social Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Theoretical Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language SEMIEMPIRICAL METHODS; OPTIMIZATION; PARAMETERS Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/42563