Saddlequat: A 6helquat captured on its racemization pathway

Adriaenssens, L.a and Severa, L.a and Koval, D.a and Císa�ová, I.b and Belmonte, M.M.c and Escudero-Adán, E.C.c and Novotná, P.d and Sázelová, P.a and Vávra, J.a and Pohl, R.a and Šaman, D.a and Urbanová, M.e and Kaši�ka, V.a and Teplý, F.a (2011) Saddlequat: A 6helquat captured on its racemization pathway. Chemical Science, 2 (12). pp. 2314-2320. ISSN 20416520

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Item Type:Article
Item Status:Live Archive

Abstract

A dicationic 6helicene congener captured on the racemization pathway in its saddle-shaped geometry is introduced. Synthesis, structure, resolution, and dynamic properties of this chiral 6saddlequat in-between and its highly stereocontrolled transformation into enantiopure 6helquat are discussed and demonstrated. The dynamic aspects established by experiment and supported by detailed DFT-D calculations are presented visually in the form of a movie (electronic table-of-contents and electronic supplementary information). The title 6saddlequat was found to be an isolable chiral species on the entirely chiral enantiomerization pathway of a 6helquat that is discussed as an example of Mislow's "rubber glove" molecule. © The Royal Society of Chemistry 2011.

Additional Information:cited By 21 The final published version of this article can be accessed online at: http://pubs.rsc.org/en/content/articlelanding/2011/sc/c1sc00468a#!divAbstract
Keywords:Chiral species, Dynamic aspects, Dynamic property, Electronic supplementary informations, Enantiomerization, Enantiopure, Helicenes, Racemization pathway, Rubber gloves, Stereochemistry
Subjects:F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Chemistry
ID Code:22741
Deposited On:25 Jul 2018 10:40

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