The conformations of allylic alcohols in solution from FT-i.r. OH stretching vibration measurements |
| |
| Institution: | 1. Key Laboratory of Green Processing and Functional Textiles of New Textile Materials, Ministry of Science and Technology, Wuhan Textile University, Wuhan 430073, PR China;2. Faculty of Materials Science and Engineering, Hubei University, Wuhan 430062, PR China;1. Department of Energy Systems Engineering, Faculty of Engineering and Architecture, Sinop University, 57000 Sinop, Turkey;2. Department of Chemistry, Faculty of Science, Hacettepe University, 06800 Ankara, Turkey;3. Department of Chemistry, Faculty of Gazi Education, Gazi University, Teknikokullar, 06500 Ankara, Turkey;4. Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey;1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganov Str., Minsk 220072, Belarus;2. Department of Chemistry, Dr. B. R. Ambedkar National Institute of Technology, Jalandhar 144011, Punjab, India;3. Department of Organic Chemistry, University of Mazandaran, 47416 Babolsar, Iran;4. Department of Chemistry, Islamic Azad University-Rasht Branch, P.O. Box 41335-3516, Rasht, Iran;1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganov Str, Minsk 220072, Belarus;2. Institute of Chemistry of New Materials, National Academy of Sciences of Belarus, 36 Skarina Str., Minsk 220141, Belarus;3. Young Researchers and Elite Club, Gorgan Branch, Islamic Azad University, Gorgan, Iran;4. Department of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan, Iran;1. Department of Industrial Engineering. University of Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano (SA), Italy;2. Institute of Polymers, Composites and Biomaterials (IPCB – CNR) Piazzale E. Fermi 1, 80055 Portici (Na), Italy;3. Department of Engineering. University of Sannio, Piazza Roma, 82100 Benevento, Italy |
| |
| Abstract: | The distribution of conformations of allylic alcohols in CCl4 differs from that in the vapour phase and from ab initio calculations. FT-i.r. measurements of the OH stretching vibrations show two peak maxima which can be resolved by band splitting techniques. The predominant conformations of allylic alcohols are intramolecularly hydrogen bonded, with a conformation gauche (G or G′) with respect to rotation about the CO bond and eclipsed (E or E′) with respect to rotation about the CC bond. In contrast with vapour phase data and ab initio calculations, no other hydrogen bonded conformations have been identified.For primary alcohols, the shoulder to the higher wavenumber side can be unequivocally assigned to conformations in which the OH is free, with a trans (T) conformation with respect to rotation about the CO bond.The secondary allylic alcohols exhibit no bands that can be attributed to free OH conformations except in the case of severe steric interaction in the eclipsed (E) conformation.In accordance with our previous work on solvent interactions with the OH group, the contrast with the vapour state assignments are interpreted in terms of an interaction of the solvent with the OH proton which destabilizes the hydrogen bond. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
