Premium
Quantitative Analysis of Intermolecular Interactions in 3‐Cyano‐2‐Pyridones: Evaluation through Single Crystal X‐ray Diffraction and Density Functional Theory
Author(s) -
Rai Sunil K.,
Sierański Tomasz,
Khanam Shaziya,
Kumar Krishnan Ravi,
Sridhar Balasubramanian,
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.201800652
Subject(s) - stacking , intermolecular force , tautomer , density functional theory , derivative (finance) , crystallography , chemistry , nitrile , ring (chemistry) , crystal structure , non covalent interactions , single crystal , computational chemistry , molecule , hydrogen bond , stereochemistry , organic chemistry , financial economics , economics
A series of 2‐pyridones and their methyl derivatives has been studied in term of noncovalent interactions and molecular packing properties. These structural characteristics were then correlated with the quantitative analysis of the intermolecular interactions governing those compounds in three dimensional net. The electronic effect over the 2‐pyridone ring on the packing property was analysed by locking the tautomers. The SC‐XRD revealed that 4,6‐dimethyl‐3‐cyano‐2‐pyridone and its O‐methyl derivative owned the layered arrangement, while N‐methyl derivative possessed the corrugated arrangement with persistent of stacking between two pyridone rings. However, 4‐phenyl‐6‐methyl‐3‐cyano‐2‐pyridone and its N‐methyl derivative showed the reverse face‐to‐face stacking due to modest torsion of bi‐aryl rings. Similarly, 6‐phenyl‐4‐methyl‐3‐cyano‐2‐pyridone has also shown reverse face‐to‐face stacking while its N‐methyl derivative stacking between pyridone ring and nitrile group was observed. Further, quantitative analysis of intermolecular interactions was done through Hirshfeld surface analysis and density functional theory.