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Molecules 2009, 14(4), 1546-1560; doi:10.3390/molecules14041546

Pseudo-cyclic Face-to-face Rigid Structure Caused by the Intramolecular Ion Pair Effect

1,* , 2
1 Department of Chemistry, Shaoguan University, Shaoguan 512005, P. R. China 2 School of Pharmaceutical Science, Sun Yat-Sen University, Guangzhou 510275, People’s Republic of China
* Author to whom correspondence should be addressed.
Received: 14 March 2009 / Revised: 9 April 2009 / Accepted: 10 April 2009 / Published: 14 April 2009
(This article belongs to the Special Issue Coumarins and Xanthones)
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Six 3-methylpyridine zwitterions and six quinoline zwitterions were synthesized through the reaction of 4-hydroxycoumarins, p-benzoquinone and the corresponding N-aromatics. The novel pseudo-cyclic face-to-face rigid structure of the zwitterion was elucidated by 1H-NMR at different temperatures, and assumed to be caused by both the intramolecular ion pair attraction and the steric interaction.
Keywords: 4-Hydroxycoumarins; Zwitterion; Molecular structure 4-Hydroxycoumarins; Zwitterion; Molecular structure
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Zhang, S.-L.; Huang, Z.-S.; Gu, L.-Q. Pseudo-cyclic Face-to-face Rigid Structure Caused by the Intramolecular Ion Pair Effect. Molecules 2009, 14, 1546-1560.

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