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Chirality of 20‐membered unclosed cryptand: Macroring distortion via lariat arm modification
Author(s) -
Jurczak Janusz,
Sobczuk Adam,
Dąbrowa Kajetan,
Lindner Marcin,
Niedbała Patryk,
Stepniak Pawel
Publication year - 2018
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22797
Subject(s) - chemistry , cryptand , chirality (physics) , stereochemistry , crystallography , solid state , organic chemistry , ion , chiral symmetry breaking , physics , nambu–jona lasinio model , quark , quantum mechanics
Some of 19‐membered unclosed cryptands were recognized as chiral species in a solid state. While, in terms of 20‐membered macrocycle, we tune the lariat arm, developing the synthesis of α‐ and β‐naphthyl terminated moieties to gain the structural control over chirality phenomena of these systems. Indirect synthetic approach delineates the way to reach both target structures. Solely, macrocycle functionalized with the β‐naphthyl group is capable of desirable interactions with the frame of entity inducing its stronger bending that leads to the chiral crystals formation. Their structural features were examined by single crystal X‐ray diffraction and chiroptical method, represented by ECD/UV spectroscopy.