Tunable recognition of the steroid alpha-face by adjacent pi-electron density.

Proceedings of the National Academy of Sciences of the United States of America
T FriscićP G Karamertzanis

Abstract

We report a previously unknown recognition motif between the alpha-face of the steroid hydrocarbon backbone and pi-electron-rich aromatic substrates. Our study is based on a systematic and comparative analysis of the solid-state complexation of four steroids with 24 aromatic molecules. By using the solid state as a medium for complexation, we circumvent solubility and solvent competition problems that are inherent to the liquid phase. Characterization is performed using powder and single crystal X-ray diffraction, infrared solid-state spectroscopy and is complemented by a comprehensive cocrystal structure prediction methodology that surpasses earlier computational approaches in terms of realism and complexity. Our combined experimental and theoretical approach reveals that the alpha...pi stacking is of electrostatic origin and is highly dependent on the steroid backbone's unsaturated and conjugated character. We demonstrate that the alpha...pi stacking interaction can drive the assembly of molecules, in particular progesterone, into solid-state complexes without the need for additional strong interactions. It results in a marked difference in the solid-state complexation propensities of different steroids with aromatic molecule...Continue Reading

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Citations

Oct 1, 2014·Faraday Discussions·William Jones, Mark D Eddleston
Nov 26, 2015·Advanced Materials·Ryota KabeChihaya Adachi
Nov 7, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Huahui ZengXiangxiang Wu
Nov 18, 2015·Journal of Chemical Theory and Computation·Matthew HabgoodConstantinos C Pantelides
Oct 29, 2014·Journal of the American Chemical Society·Tanya K RonsonJonathan R Nitschke
Jun 14, 2011·Journal of Chemical Theory and Computation·A V KazantsevC C Pantelides

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