Events The 8th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

10.3390/ecsoc-8-01996

This submission belongs to the session f. Supramolecular Chemistry of the event The 8th International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Nov, 2004

Citation

Víctor H. Soto Tellini, Aida Jover Ramos, Juan V. Trillo Novo, Francisco Meijide, Jorge Carrazana G., José Vázquez Tato, Can Guest Hydrophobicity Guide the Entrance into the Host in the Formation of an Inclusion Complex?, in Proceedings of The 8th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2004, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-8-01996

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Can Guest Hydrophobicity Guide the Entrance into the Host in the Formation of an Inclusion Complex?

Víctor H. Soto Tellini ¹

Aida Jover Ramos ¹

Juan V. Trillo Novo ¹

Francisco Meijide ¹

Jorge Carrazana G. ¹

José Vázquez Tato ¹

1. Departamento de Química Física, Universidad de Santiago de Compostela, Facultad de Ciencias, Aptdo. 280, 27080-Lugo, Spain

Abstract

The complexation of a dihydroxy bile salt derivative (sodium 3-cetocholate; 3CC), by y-cyclodextrin (?-CD), has been studied by using 1D and 2D-NMR techniques. 3CC forms a 1:1 complex with ?-CD, with a value of (2.24+0.31)×103M-1 for the equilibrium constant. Contrary the complexation of natural bile salts by ?-CD, in which the bile salt enters into the cyclodextrin cavity by its side chain, in the present case, ROESY experiments have clearly stated that the steroid nucleus enters into the cavity by its A ring. It is proposed that this fact is a consequence of the modification of the hydrophobicity of the guest due to the substitution of the 3-hydroxyl group (present in natural bile salts) by the ceto group in 3CC.

Keywords

n/a

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