A quantum chemical approach towards understanding stability and tautomerism of 2-imino-2H-pyran derivatives
The ring-chain tautomerism of 2-imino-2 H -pyran derivatives annelated with an aromatic or aliphatic ring and their transformation into corresponding 2-pyridons were theoretically studied based on the relative stabilities of two series of model isomers calculated by the DFT B3LYP/aug-cc-pVDZ method....
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| Veröffentlicht in: | RSC advances 2016, Vol.6 (57), p.52201-52211 |
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| container_title | RSC advances |
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| creator | Vodolazhenko, Maria A. Gorobets, Nikolay Yu Zhikol, Oleg A. Desenko, Sergey M. Shishkin, Oleg V. |
| description | The ring-chain tautomerism of 2-imino-2
H
-pyran derivatives annelated with an aromatic or aliphatic ring and their transformation into corresponding 2-pyridons were theoretically studied based on the relative stabilities of two series of model isomers calculated by the DFT B3LYP/aug-cc-pVDZ method. This approach, augmented by the analysis of specific interactions between the solute and solvent molecules (DMSO or acetone) in 1 : 1 complexes and simulation of the bulk solvent medium by PCM, allowed a good agreement with the experimental data for 2-imino-2
H
-coumarines and explained their ring-chain tautomerism in different media. The main reason governing the stabilization of the open-chain isomers was found to be the specific intermolecular interaction of the hydroxyl groups of these isomers with a solvent molecule. |
| doi_str_mv | 10.1039/C6RA08873B |
| format | Article |
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H
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H
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| fulltext | fulltext |
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| ispartof | RSC advances, 2016, Vol.6 (57), p.52201-52211 |
| issn | 2046-2069 2046-2069 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008- |
| title | A quantum chemical approach towards understanding stability and tautomerism of 2-imino-2H-pyran derivatives |
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