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Conformational Simulation of Sulfamethizole by Molecular Complexation and Insights from Charge Density Analysis: Role of Intramolecular S center dot center dot center dot O Chalcogen Bonding

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Title Conformational Simulation of Sulfamethizole by Molecular Complexation and Insights from Charge Density Analysis: Role of Intramolecular S center dot center dot center dot O Chalcogen Bonding
 
Creator THOMAS, SP
VECCHAM, SPKP
FARRUGIA, LJ
ROW, TNG
 
Subject RECEPTOR ANTAGONIST C30H30N6O3S
EXPERIMENTAL ELECTRON-DENSITY
NEUTRON-DIFFRACTION
HIRSHFELD SURFACES
INTERMOLECULAR INTERACTIONS
SUPRAMOLECULAR CHEMISTRY
TAUTOMERIC PREFERENCE
CRYSTAL-STRUCTURE
HYDROGEN-BONDS
DERIVATIVES
 
Description Intramolecular S center dot center dot center dot O chalcogen bonding and its potential to lock molecular conformation have been examined in the crystal forms of sulfamethizole, a sulfonamide antibiotic. Molecular complexes of sulfamethizole, including salts and cocrystal, have been synthesized, and their crystal structures were analyzed in order to examine the possible conformational preferences of the molecule in various ionic states and supramolecular environments (neutral/cocrystal, anionic salt, and cationic salt forms). The electrostatic potential mapped on Hirshfeld surfaces generated for these crystal forms provides insights into the possible binding modes of the drug in different environments. Further, the observed conformation locking feature has been rationalized in terms of the experimental charge density features of the intramolecular S center dot center dot O chalcogen bonding in sulfamethizole. The study quantitatively illustrates and rationalizes an intriguing case of a local minimum of molecular conformation being exclusively preferred over the global minimum, as it facilitates more efficient intermolecular interactions in a supramolecular environment.
 
Publisher AMER CHEMICAL SOC
 
Date 2016-01-15T06:22:33Z
2016-01-15T06:22:33Z
2015
 
Type Article
 
Identifier CRYSTAL GROWTH & DESIGN, 15(5)2110-2118
1528-7483
1528-7505
http://dx.doi.org/10.1021/cg5016687
http://dspace.library.iitb.ac.in/jspui/handle/100/17921
 
Language en