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Keywords:

  • Circular dichroism;
  • vibronic coupling;
  • dimer model

Abstract

The absorption and circular dichroism (CD) spectra of (-)-2,2′-dimethyl-4,5-(1-naphthyl)-1,3-dioxolane (DND) were studied in the energy region 30,000 cm−1 to 50,000 cm−1. The DND ketal is treated as a naphthalene dimer and its spectra are interpreted in terms of a vibronic dimer model which includes the 1La and 1Bb states of the naphthalene chromophore. To fix the most stable conformation of DND molecule, the MNDO/AM1, RHF/6-31G, and SVWN5, BPW91 methods are employed with 6-31G and 6-31G(d',p') basis sets. All the methods are shown to yield the DND geometry that is entirely consistent with the CD and absorption spectra studied. Chirality 14:274–283, 2002. © 2002 Wiley-Liss, Inc.