[6]Saddlequat: a [6]helquat captured on its racemization pathway

0363302 - ÚOCHB 2012 RIV GB eng J - Článek v odborném periodiku
Adriaenssens, Louis - Severa, Lukáš - Koval, Dušan - Císařová, I. - Belmonte, M. M. - Escudero-Adán, E. C. - Novotná, P. - Sázelová, Petra - Vávra, Jan - Pohl, Radek - Šaman, David - Urbanová, M. - Kašička, Václav - Teplý, Filip
[6]Saddlequat: a [6]helquat captured on its racemization pathway.
Chemical Science. Roč. 2, č. 12 (2011), s. 2314-2320. ISSN 2041-6520. E-ISSN 2041-6539
Grant CEP: GA ČR GA203/09/1614; GA ČR GAP207/10/2391; GA ČR(CZ) GA203/08/1428; GA ČR GP203/09/P485
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: dynamic stereochemistry * kinetic [2+2+2] cycloaddition * DFT and spectroscopy
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 7.525, rok: 2011

A dicationic [6]helicene congener captured on the racemization pathway in its saddle-shaped geometry is introduced. 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 [6]saddlequat was found to be an isolable chiral species on the entirely chiral enantiomerization pathway of a [6]helquat that is discussed as an example of Mislow’s ‘‘rubber glove’’ molecule.
Trvalý link: http://hdl.handle.net/11104/0199281