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Steric group enforced aromatic cyclic trimer conformer in tripodal molecules

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Title Steric group enforced aromatic cyclic trimer conformer in tripodal molecules
 
Creator SATHIYASHIVAN, SD
SHANKAR, B
RAJAKANNU, P
VISHNOI, P
MASRAM, DT
SATHIYENDIRAN, M
 
Subject SMALL BENZENE CLUSTERS
PI-INTERACTIONS
DENSITY
TETRAMER
PROTEINS
EXCHANGE
THERMOCHEMISTRY
BENZIMIDAZOLE
ENERGIES
LIGANDS
 
Description A family of tripodal molecules (1-6) with/without steric ethyl groups at the central benzene scaffold and with furan/thiophene/pyridyl group at the 2-position of the benzimidazolyl unit was synthesised. Compounds 1-6 were characterized by elemental analysis and NMR spectroscopy. Compounds 1, 3, and 5 were further characterized by single crystal X-ray diffraction analysis. The molecular structures of 1 and 4 were optimized using density functional theory (DFT) calculations. X-ray and H-1 NMR studies reveal that the introduction of three ethyl groups into a central benzene scaffold of furan/thiophene/pyridyl substituted benzimidazolyl based tripodal molecules enhances the edge-to-face C-H/p interactions, thereby favouring the aromatic cyclic trimer motif, in solution and the solid state. The unsubstituted central benzene scaffold allows the furan/thiophene substituted benzimidazolyl units in the tripodal molecules to move freely thereby weakening the edge-to-face C-H/p interactions between the aromatic cyclic trimer motif. Molecular modelling calculations indicate that the energy minimized structures of the tripodal molecules adopt a symmetric cyclic aromatic motif conformation.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2016-01-15T07:19:35Z
2016-01-15T07:19:35Z
2015
 
Type Article
 
Identifier RSC ADVANCES, 5(91)74705-74711
2046-2069
http://dx.doi.org/10.1039/c5ra05151g
http://dspace.library.iitb.ac.in/jspui/handle/100/18033
 
Language en