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Unsubstituted Oxacalix[ n ]arenes ( n =4 and 8): A Conformational Study in Solution and Solid State and Interaction Studies with Aromatic Guests
Author(s) -
Peterson Anna,
Kaabel Sandra,
Kahn Iiris,
Pehk Tõnis,
Aav Riina,
Adamson Jasper
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801590
Subject(s) - chemistry , supramolecular chemistry , aromaticity , molecule , benzoic acid , calixarene , titration , solid state , ferrocene , host–guest chemistry , crystallography , stereochemistry , crystal structure , computational chemistry , organic chemistry , electrode , electrochemistry
We present single crystal structures of unsubstituted oxacalix[4]arene and oxacalix[8]arene macrocycles and investigate the weak supramolecular interactions that govern their packing in the solid state. We further show that the unsubstituted oxacalix[4]arene shows weak complexation with two aromatic guest species, benzoic acid and ferrocene, in CDCl 3 , whereas the oxacalix[8]arene host does not complex with these guest molecules. We also present NMR titration experiments with non‐aromatic acids and DFT calculations that signify the importance of π‐π interactions for complexation with benzoic acid. Weak complexation is also observed between electron‐rich aromatic guest molecules and the unsubstituted oxacalix[4]arene host.