Molecular Geometry as a Source of Chemical Information. 5. Substituent Effect on Proton Transfer in Para-Substituted Phenol Complexes with Fluoridea B3LYP/6-311+G Study
The simplified model system [p-X−PhO···H···F]-, where −X are −NO, −NO2, −CHO, −H, −CH3, −OCH3, and −OH, with various O···F distance was used to simulate the wide range of the H-bond strength. Structural changes due to variation of the substituent as well as the H-bond strength are well monitored by...
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| Veröffentlicht in: | Journal of chemical information and modeling 2005-05, Vol.45 (3), p.652-656 |
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| container_title | Journal of chemical information and modeling |
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| creator | Krygowski, Tadeusz M Szatyłowicz, Halina Zachara, Joanna E |
| description | The simplified model system [p-X−PhO···H···F]-, where −X are −NO, −NO2, −CHO, −H, −CH3, −OCH3, and −OH, with various O···F distance was used to simulate the wide range of the H-bond strength. Structural changes due to variation of the substituent as well as the H-bond strength are well monitored by the changes in the aromaticity index HOMA and by two empirical measures of the H-bond strengththe 1H NMR chemical shift of proton involved and the C−O bond length. Changes in H-bonding strengths and the position of proton transfer while shortening the O···F distance are well described by the Hammett equation. |
| doi_str_mv | 10.1021/ci049633d |
| format | Article |
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| subjects | Chemical compounds Computer based modeling Geometry Molecular structure |
| title | Molecular Geometry as a Source of Chemical Information. 5. Substituent Effect on Proton Transfer in Para-Substituted Phenol Complexes with Fluoridea B3LYP/6-311+G Study |
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