Tailoring the key in a molecular lock-and-key model system: the propylene oxide...2-fluoroethanol complex

Journal of the American Chemical Society
Nicole Borho, Yunjie Xu

Abstract

The conformational isomerism of the propylene oxide (PO)...2-fluoroethanol (FE) complex has been investigated using molecular beam Fourier-transform microwave spectroscopy complemented with high level ab initio calculations. Rotational transitions of three different binary conformers have been observed experimentally. On the basis of the agreement of the experimental and calculated rotational constants, they could be identified as the three most stable structures, anti G-g+, anti G+g-, and syn G+g-. All the observed structures exhibit a primary O-H...O hydrogen bond, an intramolecular O-H...F hydrogen bond and two secondary intermolecular C-H...F contacts. The two anti conformers, with FE and the PO methyl group on the opposite sides of the oxirane ring, show higher abundances than the syn conformer. In all three observed conformers, FE remains approximately in its favorable compact gauche conformation. The monofluorination of the molecular lock-and-key model system PO...ethanol increases not only the number of possible binary conformers, but also the discrimination energy among them. The superior discrimination ability of FE as compared to ethanol classifies it as a tailored key to the PO lock.

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Citations

Jan 22, 2013·Chirality·Elfi KrakaDieter Cremer
Mar 18, 2016·Chemical Reviews·Maurizio Becucci, Sonia Melandri
Dec 2, 2008·Chemistry : a European Journal·Xunchen LiuYunjie Xu
Jul 29, 2010·Chemistry : a European Journal·Duncan W BruceAdrian C Whitwood
Jun 28, 2011·Physical Chemistry Chemical Physics : PCCP·Sonia Melandri
Dec 19, 2012·Physical Chemistry Chemical Physics : PCCP·Fumie X SunahoriYunjie Xu
Apr 20, 2019·Chemistry : a European Journal·Marcos JuanesAlberto Lesarri
Aug 6, 2011·Acta Crystallographica. Section C, Crystal Structure Communications·Goverdhan MehtaMeenu Thangam
Apr 30, 2017·Physical Chemistry Chemical Physics : PCCP·Wenyuan HuangYunjie Xu
Jan 17, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Fan XieYunjie Xu
Jun 5, 2014·The Journal of Physical Chemistry Letters·Javix Thomas, Yunjie Xu

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