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Issue 9, 2008
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Investigation on the flexibility of chiral tricyclic derivatives

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Abstract

In the perspective of generating libraries for broad screening purposes, the inversion barrier of enantiomeric conformers of various tricyclic compounds, characterized by a seven-membered ring featuring a lactam group with two aromatics condensed at its opposite sides, has been investigated by ab initio calculations and NMR spectroscopy. Solid-state structure characterizations by single-crystal X-ray diffraction have been also carried out. The aim was to assess if moving from ethers to sulfides and sulfones derivatives, causes the racemization barrier to vary. Investigation was also extended to thiolactam congeners. Structural and electronic effects were investigated on the energetics of the inversion process and structure-property relationships evidenced. Results suggest that the ring inversion of the oxo derivatives is easier with respect to the corresponding S/SO2 ones. Also amide molecules have, on the whole, smaller barriers with respect to the corresponding thioamide ones.

Graphical abstract: Investigation on the flexibility of chiral tricyclic derivatives

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Publication details

The article was received on 29 Jan 2008, accepted on 18 Apr 2008 and first published on 30 Jun 2008


Article type: Paper
DOI: 10.1039/B801569D
Citation: New J. Chem., 2008,32, 1617-1627
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    Investigation on the flexibility of chiral tricyclic derivatives

    M. Altamura, P. Dapporto, A. Guidi, N. J. S. Harmat, L. Jierry, E. Libralesso, P. Paoli and P. Rossi, New J. Chem., 2008, 32, 1617
    DOI: 10.1039/B801569D

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