Proton transfer from H2O to p-substituted anilide anion: can the size of water cluster influence the N-⋅⋅⋅H–OH→N–H⋅⋅⋅OH- switching
| Autor: | Hossein Roohi, Behnaz Moghadam |
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| Rok vydání: | 2011 |
| Předmět: |
Electron density
Proton Stereochemistry Chemistry Organic Chemistry Solvation Substituent Interaction energy Catalysis Computer Science Applications Ion Inorganic Chemistry Crystallography chemistry.chemical_compound Computational Theory and Mathematics Atom Water cluster Physical and Theoretical Chemistry |
| Zdroj: | Journal of Molecular Modeling. 18:1313-1324 |
| ISSN: | 0948-5023 1610-2940 |
| DOI: | 10.1007/s00894-011-1156-7 |
| Popis: | The effects of the H2O cluster size and the substituent (X=H, Me, OMe, CHO, NO and NO2) in the para position of anilide ion on the HN-⋅⋅⋅H–OH→HN–H⋅⋅⋅OH- switching were investigated by means of B3LYP and MP2 methods. The changes in the H-bond strength due to variation of the substituent and H2O cluster size were well monitored by changes in the interaction energy, structural parameter, electron density topology, natural charge, charge transfer and percentage of p-character of N atom in the C–N bond. The HN-⋅⋅⋅H–OH→HN–H⋅⋅⋅OH- switching was enhanced by an increase in the extent of solvation and the insertion of the electron-donating substituents in the para position. The results demonstrate that the strength of the HN-∙∙∙HO H-bond increases and that of NH∙∙∙OH- H-bond decreases by electron-donating substituents. The reverse situations were found for electron-accepting substituents. |
| Databáze: | OpenAIRE |
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