Unprecedented pi...pi interaction between an aromatic ring and a pseudo-aromatic ring formed through intramolecular H-bonding in a bidentate Schiff base ligand: crystal structure and DFT calculations

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Authors	DUTTA Arpan JANA Atish Dipankar GANGOPADHYAY Sumana DAS Kalyan Kumar MAREK Jaromír MAREK Radek BRUS Jiří ALI Mahammad
Year of publication	2011
Type	Article in Periodical
Magazine / Source	Physical Chemistry Chemical Physics
MU Faculty or unit	Central European Institute of Technology
Citation
Web	DOI: 10.1039/c1cp21047e
Doi	http://dx.doi.org/10.1039/c1cp21047e
Field	Physical chemistry and theoretical chemistry
Keywords	Pi-pi interaction; X-ray diffraction; Solid-state NMR; Molecular orbitals
Attached files	PCCP11_13_15845.pdf
Description	A combination of a single crystal X-ray diffraction study and density functional theory calculations has been applied to a bidentate Schiff base compound to elucidate different cooperative non-covalent interactions involved in the stabilization of the keto form over the enol one in the solid state. The single crystal X-ray structure reveals a remarkable supramolecular assembly of the keto form through a cyclic hydrogen bonded dimeric motif. The most interesting feature in the supramolecular assembly is the formation of a ‘dimer of dimer’ motif by pi-pi, CH-pi and N-O/O-O interactions in which the pi-pi interaction involving the aromatic phenyl ring and the intramolecularly hydrogen bonded pseudo-aromatic ring of the keto form lying just above or below the phenyl ring of the other dimer seems to be unprecedented.
Related projects:	Proteins in metabolism and interaction of organisms with the environment Molecular basis of cell and tissue regulations NMR spektroskopie pevného stavu organických molekul, polymorfů, solvátů a komplexů CEITEC - Central European Institute of Technology