Thermodynamic Evaluation of Aromatic CH/π Interactions and Rotational Entropy in a Molecular Rotor

A molecular rotor built with a stator formed by two rigid 9β-mestranol units having a 90° bent angle linked to a central phenylene rotator has an ideal structure to examine aromatic CH/π interactions. Energies and populations of the multiple solution conformations from quantum-mechanical calculation...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-02, Vol.137 (6), p.2175-2178
Main Authors: Pérez-Estrada, Salvador, Rodrı́guez-Molina, Braulio, Xiao, Leilei, Santillan, Rosa, Jiménez-Osés, Gonzalo, Houk, K. N, Garcia-Garibay, Miguel A
Format: Article
Language:English
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Summary:A molecular rotor built with a stator formed by two rigid 9β-mestranol units having a 90° bent angle linked to a central phenylene rotator has an ideal structure to examine aromatic CH/π interactions. Energies and populations of the multiple solution conformations from quantum-mechanical calculations and molecular dynamics simulations were combined with variable-temperature (VT) 1H NMR data to establish the enthalpy of this interaction and the entropy associated with rotation about a single bond. Rotational dynamics in the solid state were determined via VT cross-polarization magic-angle spinning 13C NMR spectroscopy.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja512053t