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Int. J. Mol. Sci. 2014, 15(6), 9844-9858;

Qualitative Analysis of the Helical Electronic Energy of Inherently Chiral Calix[4]arenes: An Approach to Effectively Assign Their Absolute Configuration

Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of Pharmacy, Basic Medical Research Center, Tianjin Medical University, Tianjin 300070, China
MOE Laboratory of Bioinorganic and Synthetic Chemistry/KLGHEI of Environment and Energy Chemistry, State Key Laboratory of Optoelectronic Materials and Technologies, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China
Authors to whom correspondence should be addressed.
Received: 27 March 2014 / Revised: 4 May 2014 / Accepted: 12 May 2014 / Published: 3 June 2014
(This article belongs to the Special Issue Molecular Science for Drug Development and Biomedicine)
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For all microhelices on aromatic rings of inherently chiral calix[4]arene, an expression was derived from one approximation and one hypothesis on the basis of the electron-on-a-helix model of Tinoco and Woody as follows: 1/E = μ (HK Δα2) , where μ = 1 for the right-handed microhelix and μ = −1 for the left-handed microhelix; and H and K are constant and greater than zero. The expression correlates microhelical electronic energy (E) with the atom polarizability difference (Δα) on both microhelix ends, which intuitively and clearly shows the impact of helical substituent polarizability on helical electronic energy. The case analysis almost entirely proves that the qualitative analysis of the helical electronic energy of inherently chiral calix[4]arenes with the expression is scientific and can be used to effectively assign their absolute configuration View Full-Text
Keywords: inherently chiral; calix[4]arene; helix theory; absolute configuration inherently chiral; calix[4]arene; helix theory; absolute configuration

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Zheng, S.; Chang, M.-L.; Zhou, J.; Fu, J.-W.; Zhang, Q.-W.; Li, S.-Y.; Qiao, W.; Liu, J.-M. Qualitative Analysis of the Helical Electronic Energy of Inherently Chiral Calix[4]arenes: An Approach to Effectively Assign Their Absolute Configuration. Int. J. Mol. Sci. 2014, 15, 9844-9858.

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