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Triarylmethanols with Bulky Aryl Groups and the NOESY/EXSY Experimental Observation of a Two-Ring-Flip Mechanism for the Helicity Reversal of Molecular Propellers Full article

Journal European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Output data Year: 2012, Volume: 2012, Number: 3, Pages: 623-629 Pages count : DOI: 10.1002/ejoc.201101243
Tags Isomerization; Chirality; NMR spectroscopy; 2D NOESY/EXSY; Epimerization mechanism; Activation parameters
Authors Tormyshev Victor M. 1,2 , Genaev Alexander M. 1 , Sal'nikov Georgy E. 1 , Rogozhnikova Olga Yu 1 , Troitskaya Tatiana I. 1 , Trukhin Dmitry V. 1 , Mamatyuk Victor I. 1 , Fadeev Dmitry S. 1 , Halpern Howard J. 3
Affiliations
1 (Данные Web of science) Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk State Univ, Dept Nat Sci, Novosibirsk 630090, Russia
3 (Данные Web of science) Univ Chicago, Dept Radiat & Cellular Oncol, Ctr EPR Imaging Vivo Physiol, Chicago, IL 60637 USA

Abstract: Triarylmethanols - the direct precursors of persistent trityl radicals - are racemic mixtures of chiral three-bladed molecular propellers. Depending on the bulkiness of the aryl groups, they exhibit various tendencies to interconvert, and the half-life of room-temperature racemization varies between 8.4 h and 1.32 years. NOESY/EXSY experiments performed on two representative models strongly support the two-ring flip mechanism for the configurational interchange.
Cite: Tormyshev V.M. , Genaev A.M. , Sal'nikov G.E. , Rogozhnikova O.Y. , Troitskaya T.I. , Trukhin D.V. , Mamatyuk V.I. , Fadeev D.S. , Halpern H.J.
Triarylmethanols with Bulky Aryl Groups and the NOESY/EXSY Experimental Observation of a Two-Ring-Flip Mechanism for the Helicity Reversal of Molecular Propellers
European Journal of Organic Chemistry. 2012. V.2012. N3. P.623-629. DOI: 10.1002/ejoc.201101243 WOS Scopus РИНЦ
Files: Full text from publisher
Dates:
Published online: Nov 28, 2011
Published print: Jan 1, 2012
Identifiers:
Web of science WOS:000299295700023
Scopus 2-s2.0-84855973757
Elibrary 17974071
OpenAlex W2152271914
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