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Updated: Sep 22, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
NMR studies of inclusion complexes: naphthalene and natural cyclodextrins
Sylwia Jopa1, Jacek Wójcik2, Andrzej Ejchart2
1Faculty of Chemistry, Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, Poland. lyam@chem.uw.edu.pl.
Abstract:
Inclusion complexes of naphthalene (NP) with cyclodextrins (CD) have been investigated so far using non-NMR techniques resulting in inconsistent data. Here, the first application of high-field NMR spectroscopy in combination with a precise analysis of the results has allowed us to determine accurately the stoichiometry of complexes and their association constants. Titration measurements have been performed by 1H NMR spectroscopy in D2O at a magnetic field B0 of 18.8 T. NP and αCD form a 1 : 2 complex in which a single NP molecule is closed in a capsule made up of two αCD macrocycles. NP and βCD build coexisting 2 : 1 and 2 : 2 complexes with large binding constants. Larger γCD host molecules form essentially similar complexes with NP as the βCD but corresponding binding constants are smaller.
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