PMID: 11607365Feb 15, 1993Paper

Modeling the complexation of substituted benzenes by a cyclophane host in water

Proceedings of the National Academy of Sciences of the United States of America
W L Jorgensen, T B Nguyen

Abstract

Monte Carlo statistical mechanics simulations have been used to study the complexation of disubstituted benzenes by Diederich's octamethoxy tetraoxaparacyclophane host. Relative free energies of binding were obtained in water at 25 degrees C for benzene, p-xylene, p-cresol, p-dicyanobenzene, and hydroquinone from statistical perturbation theory. The computed results agree well with experimental data, including the binding affinity of benzene, which was determined after the calculations were completed. The computed structures for the complexes reveal details that are important for understanding the order of binding affinities. It is found that hydroquinone protrudes from one side of the complex and participates in hydrogen bonds between one hydroxyl group and two water molecules and in an intracomplex hydrogen bond between the other hydroxyl group and ether oxygens. The calculations also show a clear preference for binding p-cresol with the hydroxyl group hydrated rather than inside the host's cavity.

References

Apr 2, 1991·Biochemistry·B Tidor, M Karplus
Jan 1, 1989·Annual Review of Biophysics and Biophysical Chemistry·D L Beveridge, F M DiCapua
Feb 1, 1986·Proceedings of the National Academy of Sciences of the United States of America·T P LybrandG Wipff

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Citations

Feb 7, 1998·Proceedings of the National Academy of Sciences of the United States of America·O MandelboimJ L Strominger
Mar 23, 2010·Langmuir : the ACS Journal of Surfaces and Colloids·Yumin LengFrauke Gräter
Dec 26, 2001·Chemical Reviews·Modesto Orozco, F. Javier Luque

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