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Study of Conformational and Supramolecular Structural Stability of Propylene‐Bridged 2‐Pyridone Dimers
Author(s) -
Rai Sunil K.,
Khanam Shaziya,
Tewari Ashish K.
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.201702565
Subject(s) - supramolecular chemistry , stacking , crystallography , intramolecular force , non covalent interactions , chemistry , differential scanning calorimetry , crystal structure , density functional theory , stereochemistry , molecule , computational chemistry , hydrogen bond , organic chemistry , physics , thermodynamics
In quest of the role of noncovalent interaction for the preference of inter and intramolecular stacking phenomenon, we synthesized O/O ( 1 ), N/O ( 2 ) and N/N ( 3 ) isomeric dimers of 3‐cyano‐4,6‐dimethyl‐2‐pyridone linked through propylene chain. The direct evidence of noncovalent interactions and conformation of all the three isomers were obtained by single crystal X‐ray diffraction analysis and conformational stability was evaluated through density functional theory. Isomers 1 and 2 were crystallized in stable conformation while isomer 3 was crystallized in constraint geometry which was further confirmed by differential scanning calorimetry analysis. The supramolecular structure in isomer 1 showed the helical geometry, isomer 2 showed the parallel stacking and pleated structure, while isomer 3 showed only pleated structure.