(Figure Presented) Synthesis of 6-endo and 6-exomethylthio-2- endoarylbicyclo[2.2.1]heptanes was accomplished stereoselectively. The ionization energies, determined by photoelectron spectroscopy, and electrochemical oxidation potentials, determined by cyclic voltammetry, were lower for the 6-endomethylthio compounds than for their 6-exomethylthio analogues. Calculations supported the notion that facilitation of electron transfer in the 6-endomethylthio compounds results from through-space S⋯π interaction.
|Original language||English (US)|
|Number of pages||4|
|State||Published - Jan 15 2009|
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
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CCDC 725652: Experimental Crystal Structure Determination
Chung, W. J. (Creator), Ammam, M. (Creator), Gruhn, N. E. (Creator), Nichol, G. S. (Creator), Singh, W. P. (Creator), Wilson, G. S. (Creator) & Glass, R. S. (Creator), Cambridge Crystallographic Data Centre, 2009
DOI: 10.5517/ccsc34c, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccsc34c&sid=DataCite