Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 19, Pages 9949-9955Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo401825k
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Funding
- Natural Science Foundation of China
- National Ministry of Science and Technology of China [2012CB224801]
- Program for New Century Excellent Talents in University
- Fundamental Research Funds for the Central Universities
- Beijing Natural Science Foundation
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A C-1-symmerical meso-substituted ABCD-type porphyrin, [5-phenyl-10-(2-hydroxynaphthyl)-15-(4-hydroxyphenyl)porphyrinato]zinc(11) (1), has been synthesized and characterized. The molecular structure of 1 has been determined by single-crystal X-ray diffraction analysis. The complex 1 crystallins in a triclinic system with one pair of enantiomeric molecules per unit cell. Resolution of the racemic mixture has been achieved by chiral HPLC techniques. In particular, the absolute configurations of the enantiomers have been assigned from NMR spectroscopic analysis with L-Phe-OMe as the chiral solvating agent (CSA). The assignments have also been unambiguously confirmed by single-crystal X-ray diffraction analysis. The present results suggest that the CSA-NMR anisotropy strategy is applicable for the stereochemistry determination of chiral host guest complexes with multiple intermolecular interactions In addition, the multiple intermolecular interactions between the enantiomerically pure porphyrin S-1 and L-Phe-OMe are proved in the solid state by single crystal X-ray diffraction analysis
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