Journal
TETRAHEDRON
Volume 69, Issue 50, Pages 10752-10762Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.10.016
Keywords
ORD; ECD; VCD; Vibronic features; Absolute configuration; Conformations; Phenyl hindered rotation
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Funding
- MIUR [PRIN 2010-2011 prot. 2010ERFKXL]
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Three forms of chiroptical spectroscopies, electronic circular dichroism (ECD), vibrational circular dichroism (VCD), and optical rotatory dispersion (ORD) have been employed to study the configuration and conformational properties of the three molecules: (S)-3-phenylcyclopentanone, (S)-3phenylcyclohexanone, and (S)-3-phenylcycloheptanone (including (S)-3-phenylcyclopentanone-2,2,5,5d(4) and (S)-3-phenylcyclohexanone-2,2,6,6-d(4)). ECD and VCD spectra in the mid-IR for the three molecular systems are marginally dependent on fine conformational details, as interpreted in terms of standard DFT computational methods, with common spectroscopic features to the three systems clearly identified. Accounting for vibronic coupling mechanisms reproduces the structuring of ECD n ->pi* band. The ORD curves are quite similar for the three types of molecules, but their interpretation highlights a crucial role played by conformations of the cycloalkanone ring in the case of (S)-3phenylcycloheptanone. The same conclusions are reached by considering the VCD spectra in the CHstretching region. (C) 2013 Elsevier Ltd. All rights reserved.
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