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Solution Structure of the Inclusion Complexes between Cyclodextrins and Dialkylamines: An NMR Study
Author(s) -
Lucarini Marco,
Mezzina Elisabetta,
Pedulli Gian Franco
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200012)2000:23<3927::aid-ejoc3927>3.0.co;2-z
Subject(s) - chemistry , amine gas treating , electron paramagnetic resonance , intermolecular force , spectroscopy , nuclear magnetic resonance spectroscopy , chemical shift , nitroxide mediated radical polymerization , crystallography , molecule , computational chemistry , stereochemistry , organic chemistry , nuclear magnetic resonance , polymer , physics , radical polymerization , quantum mechanics , copolymer
Abstract Interaction between chemically modified cyclodextrins (CDs) and benzyl( tert ‐butyl)amine ( 1 ), tert ‐butyl(methyl)amine ( 2 ) and benzyl(methyl)amine ( 3 ) has been investigated by NMR spectroscopy. The experimental results revealed that the complexation‐induced shifts for the reported amines were more pronounced for the carbon atoms than for the protons. These shift variations were successfully exploited for determining the association constants with heptakis(2,6‐ O ‐dimethyl)‐β‐CD, which were found to be 295, 119 and 101 M −1 for 1 , 2 and 3 , respectively. Features of the geometries of the amine/DM‐β‐CD complexes were deduced by measuring the NOE intermolecular interactions between host and guest protons. These data made it possible to elucidate fully the nature of the amine/CD complexes and provided information complementary to that previously obtained by EPR spectroscopy on the complexation of the closely related nitroxide/CD paramagnetic complexes.