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Alkali Metal- and Ammonium Picrate Extraction and Complex Forming Capabilities of d-Glucose and d-Mannose-based Lariat Ethers

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ABSTRACT

The alkali metal- and ammonium picrate extracting ability of d-glucose- and d-mannose-based 15-crown-5 ethers and related lariat ethers was investigated in dichloromethane – water system. A heteroatom was waried in the crown ether containing a 4,6-O-benzylidene-α-d-glucopyranoside unit 6, (X=O), 2 (X=S) and 8a (X=NH). Extracting ability of the latter species (8a) was excellent (97–99%) in regard of all cations (Li+, Na+, K+, Rb+, Cs+ and NH +4 ) examined, it was not, howewer, selective. Introduction of a side arm on the nitrogen atom of 8a decreased the extracting ability, but increased the selectivity. In this series of compounds (8b–f, 4), 4 with a pyridylethyl substituent allowed the extraction of sodium picrate in 72%. The glucose-based macrocycles 8a, 8e and 8f formed a stronger complex with the cations examined than the mannose-based analogues 9a, 9e and 9f, that can be explained by the all-gauche conformation of the former ones. It was pointed out that in the case of crowns with tertiary amine moieties, the basicity increases the quantity of the picrates extracted. According to complex forming measurements by FAB-MS, the best sodium ion selectivity was achieved by the γ-hydroxypropyl substituted lariat ether (8e). Possible structures of the complexes formed by the two types of monosacharides with sodium cation were evaluated by molecule modelling calculations.

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Acknowledgements

This work was supported by OTKA T 42514, T 042933 and the joint founds from the European Union and the Hungarian State (GVOP-3.2.2.-2004-07-0006/3.0).

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Authors and Affiliations

  1. Department of Organic Chemical Technology, Budapest University of Technology and Economics, P. O. Box 91, 1521, Budapest, Hungary

    PÉTER BAKÓ, ATTILA MAKÓ, GYÖRGY KEGLEVICH & TAMÁS SEFCSIK

  2. Department of Chemical Information and Technology, Budapest University of Technology and Economics, P. O. Box 91, 1521, Budapest, Hungary

    DÓRA K. MENYHÁRT

  3. Department of General and Analytical Chemistry, Budapest University of Technology and Economics, P. O. Box 91, 1521, Budapest, Hungary

    JENŐ FEKETE

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  1. PÉTER BAKÓ
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Correspondence to PÉTER BAKÓ.

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BAKÓ, P., MAKÓ, A., KEGLEVICH, G. et al. Alkali Metal- and Ammonium Picrate Extraction and Complex Forming Capabilities of d-Glucose and d-Mannose-based Lariat Ethers. J Incl Phenom Macrocycl Chem 55, 295–302 (2006). https://doi.org/10.1007/s10847-006-9051-z

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  • DOI: https://doi.org/10.1007/s10847-006-9051-z

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