Tweezer-Type Catechol and Resorcinol Derivatives: Preparation, Structures, and First Investigations Towards their Hydrogen Bonding Abilities

Abstract

Tweezer-type molecules with an ester linkage between catechol or resorcinol and linear amino acid-based urea or amide derivatives are prepared. X-ray structures of representative compounds show, that the molecules are able to form intra- as well as intermolecular hydrogen bonds. In solution this hydrogen bonding donor/acceptor ability of the tweezers can be seen, on the one hand by interaction with anionic guest species (nitrate), and on the other hand by formation of gels in the case of the urea derivatives.

Key words

amino acids - esters - hydrogen bonds - molecular recognition - supramolecular chemistry

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18

Data sets were collected with Enraf-Nonius CAD4 and Nonius KappaCCD diffractometer. Programs used: data collection EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B.V., 1998), data reduction MolEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN, absorption correction for CCD data SORTAV, structure solution SHELXS-97, structure refinement SHELXL-97 (G.M. Sheldrick, Universität Göttingen, 1997). [19] Crystallographic data (excluding structural factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 180408, 180409 and 180410. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, CambridgeCB2 1EZ, UK [fax: int. code: [phone], e-mail: [e-mail]].