Influence of the CH/π hydrogen bond on the enhancement of circular dichroism (CD) amplitude of 5,7-diene steroids: ergosterol, lumisterol, pirocarciferol, isopirocarciferol and structurally related cyclohexadienes?

New Journal of Chemistry Pub Date: 2013-04-11 DOI: 10.1039/C3NJ41148F

Abstract

Rotational strengths were calculated, by the TD-DFT (time-dependent density functional theory) method, for a series of 5,7-diene steroids, ergosterol, lumisterol, pirocarciferol, isopirocarciferol, as well as structurally related compounds such as 2,4-cholestadiene and levopimaric acid. The results were discussed in the context of the CH/π hydrogen bond; we suggest that the CH/π hydrogen bond plays an important role in the enhancement of CD amplitude of cisoid dienes.

Graphical abstract: Influence of the CH/π hydrogen bond on the enhancement of circular dichroism (CD) amplitude of 5,7-diene steroids: ergosterol, lumisterol, pirocarciferol, isopirocarciferol and structurally related cyclohexadienes
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