Correlated Rotations and Unusual Fluorescence Properties of peri-Substituted, Axially Chiral Naphthyl Ketones
✍ Scribed by Christoph Kiefl
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 368 KB
- Volume
- 2000
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
The dynamics of the two rotors in 8-(dimethylamino)naphthyl ketones possessing a tetrahedral amino group and a trigonal planar carbonyl group has been investigated by 1 H NMR spectroscopy. The dynamic system is described by an aryl-nitrogen and an aryl-carbonyl rotation and a possible amine inversion. As the two rotors, which are twisted in the ground state, are tightly interlocked, the question arises of how strongly the processes might be correlated and how strongly the electrostatic interactions would influence the barriers. In the case of the isopropyl, tert-butyl, and benzyl ketones, the rotors are coupled sufficiently strongly that correlated rotations become energetically preferred over independent rotations of the individual groups. For the methyl and trimethoxyphenyl ketone, the Ar-N and Ar-C barriers could be distinguished because of the lesser degree of inter-