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Sulfate Encapsulation in Supramolecular Structures from L ‐Asparagine‐Derived 2,5‐Diketopiperazine Scaffolds: Anion Binding
Author(s) -
Naini Santhosh Reddy,
Lalancette Roger A.,
Gorlova Olga,
Ramakrishna Kallaganti V. S.,
Yadav Jhillu Singh,
Ranganathan Subramania
Publication year - 2014
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/ejoc.201402610
Subject(s) - chemistry , supramolecular chemistry , hydrogen bond , sulfate , asparagine , ion , stoichiometry , host–guest chemistry , molecule , proton nmr , stereochemistry , combinatorial chemistry , crystallography , polymer chemistry , organic chemistry , enzyme
We report a new sulfate receptor, anchored onto 2,5‐diketopiperazine units, which results in the formation of two types of supramolecules; one in which the sulfate ion guest fits snugly into extended cavities and the other in which the guest is sandwiched between layers. In each case, the anion is held by six hydrogen bonds from the host. 1 H NMR spectroscopic solution studies enabled the construction of Job plots, and calculation of stoichiometry and association constants. These findings are of possible significance in drug design and for construction of combinatorial libraries.