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- W2571499015 abstract "Bis adducts of 2‐indanone with 1 H ‐pyrrole‐2‐carbaldehyde, 1 H ‐imidazole‐2‐carbaldehyde, 1 H ‐imidazole‐5‐carbaldehyde, and 1 H ‐indazole‐3‐carbaldehyde 3 – 6 have been synthesized and the intertwined processes of tautomeric NH proton transfer, intra‐ and intermolecular H‐bond rupture and formation, and Z/Z, Z/E , and E/E ‐isomerization have been studied by NMR and FTIR spectroscopy and by conducting DFT calculations. Pyrrole derivative 3 both in chloroform and in dimethyl sulfoxide (DMSO) exists exclusively in the form of the Z , Z ‐isomer stabilized by two intramolecular N–H ··· O hydrogen bonds. For derivatives 4 – 6 , the isomeric composition depends on the solvent so that in polar media such as DMSO and pyridine the Z , E ‐ and E , E ‐isomers predominate. The driving force for isomerization of 4 – 6 is stabilization of the Z , E ‐ and E , E ‐isomers in basic polar solvents due to formation of intermolecular NH ··· B and intramolecular C–H ··· N hydrogen bonds. The suggested mechanism of isomerization includes proton transfer from nitrogen to oxygen in the Z ‐moiety followed by rotation about the C–C bond in the formed enol and isomerization of the latter to the E ‐moiety of the ketone tautomer." @default.
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- W2571499015 date "2017-03-10" @default.
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- W2571499015 title "Molecular Structure, Intramolecular Hydrogen Bonding, Solvent-Induced Isomerization, and Tautomerism in Azolylmethylidene Derivatives of 2-Indanone" @default.
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- W2571499015 doi "https://doi.org/10.1002/ejoc.201601579" @default.
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