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The Role of Weak Interactions in Supramolecular Compounds: A Synthetic and Theoretical Study of Novel Elongated Cavitands
Author(s) -
Kégl Tímea,
Csekő György,
Mikle Gábor,
Takátsy Anikó,
Kollár László,
Kégl Tamás
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701762
Subject(s) - cavitand , cycloaddition , supramolecular chemistry , intramolecular force , chemistry , computational chemistry , resorcinol , ring (chemistry) , click chemistry , chemical shift , aromaticity , stereochemistry , crystallography , molecule , combinatorial chemistry , organic chemistry , crystal structure , catalysis
A new resorcinol‐based tetraazidocavitand ( 2 ) has been prepared via substitution reaction started from the corresponding tetrabromocavitand ( 1 ). This tetraazidocavitand was used as a starting material for azide‐alkyne cycloaddition with different alkynes and this way four novel deepened cavitands have been synthesized under mild conditions. Molecular dynamics, semiempirical PM6 and DFT PBEPBE/6‐31G(d,p) studies have been carried out for these new triazole ring containing structures to reveal the exact geometry in solution, furthermore theoretical NMR chemical shift calculations were completed at B3LYP−D3/6‐31G(d,p) GIAO level in order to compare with the experimental NMR data. QTAIM analysis at B3LYP−D3/def2‐TZVP level was performed and NCI isosurfaces were generated to reveal the potential intramolecular weak interactions between the cavitand branches.