Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/95266
Title: The syn conformers of several 2,11-dithia[3.3](1,4) naphthalenometacyclophanes: Novel preference for a conformation with parallel benzenoid rings from direct confrontation of two different modes of non-bonding interaction
Authors: Lai, Y.-H. 
Issue Date: 1989
Source: Lai, Y.-H. (1989). The syn conformers of several 2,11-dithia[3.3](1,4) naphthalenometacyclophanes: Novel preference for a conformation with parallel benzenoid rings from direct confrontation of two different modes of non-bonding interaction. Journal of the Chemical Society, Perkin Transactions 2 (6) : 643-648. ScholarBank@NUS Repository.
Abstract: 2,11-Dithia[3.3](1,4)naphthalenometacyclophane and its 9-bromo- and 9-fluoro-derivative have been synthesized. 1H and 19F n.m.r. studies have indicated that all three dithiacyclophanes prefer the syn-conformation with near-parallel stacking of aromatic rings. This conformational preference is supported by results from MMP2 calculations. The angle of tilting of the meta-bridged ring is dependent on the 9-substituent. Variable-temperature n.m.r. studies have unexpectedly shown neither a flipping of the meta-bridged ring nor a wobbling of the C-S-C bridges. Possible conformational behaviour is the continuous tilting process of the meta-bridged ring in the rigid syn-conformation. A solvent effect on the chemical shifts of both the reference protons and the fluorine has been observed.
Source Title: Journal of the Chemical Society, Perkin Transactions 2
URI: http://scholarbank.nus.edu.sg/handle/10635/95266
ISSN: 1472779X
Appears in Collections:Staff Publications

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