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Conformational Control due to Arene Interactions in Dissymmetrical Diaryl 2-Methylenepropylidene Both in Solution and Solid State

IR@CDRI: CSIR-Central Drug Research Institute, Lucknow

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Field Value
 
Creator Avasthi, Kamlakar
Shukla, Lakshmi
Kant, Ruchir
Ravikumar, Krishnan
 
Date 2015-03-30T11:42:32Z
2015-03-30T11:42:32Z
2014
 
Identifier Journal of Structural Chemistry, 2014, 55(8), 1587-1595
http://hdl.handle.net/123456789/1443
 
Description We have designed and synthesized dissymmetrical diaryl 2-methylenepropylidenes based on pyrazolo[3,4-d]pyrimidine core for studying conformational control due to arene interactions in face-to-face (offset) mode. Dissymmetrical 2-methylenepropylidene linker models (N1-N1 isomers) show intramolecular π‒π stacking (folded conformation) by 1H NMR in solution which carries over to solid state as revealed by single crystal X-ray crystallography. Corresponding, N1-N2 isomers do not show intramolecular π‒π stacking at molecular level. In addition to arene interactions crystal structures are also stabilized by intermolecular C−H…O, C−H…S or C−H…N interactions.
 
Format 561876 bytes
application/pdf
 
Language en
 
Relation CSIR-CDRI Communication No. 8703
 
Subject Arene interaction
2-Methylenepropylidene linker
Pyrazolo[3,4-d]pyrimidine
X-ray structure
 
Title Conformational Control due to Arene Interactions in Dissymmetrical Diaryl 2-Methylenepropylidene Both in Solution and Solid State
 
Type Article