Conformational Study of the Structure of dibenzo-18-crown-6. Comparison with 18-crown-6 |
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| Affiliation: | 1. Laboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna, Université de Carthage, Tunisia;2. Laboratoire des substances bio-actives, Faculté des Sciences de Bizerte 7021 Zarzouna, Université de Carthage, Tunisia;1. Department of Obstetrics and Gynecology, Wayne State University School of Medicine, Detroit, MI 48202, USA;2. Department of Computer Science, Wayne State University College of Engineering, Detroit, MI, USA;3. SJTU-Yale Joint Centre for Biostatistics, Shanghai Jiao Tong University, Shanghai, China;4. Department of Bioinformatics and Biostatistics, School of Life Sciences and Biotechnology, Shanghai Jiao Tong University, Shanghai, China;5. Perinatology Research Branch, NICHD/NIH/DHHS, Bethesda, MD, and Detroit, MI 48201, USA;6. Department of Obstetrics and Gynecology, University of Michigan, Ann Arbor, MI 48109, USA;7. Department of Epidemiology and Biostatistics, Michigan State University, East Lansing, MI 48825, USA;8. Center for Molecular Medicine and Genetics, Wayne State University, Detroit, MI 48201, USA;9. School of Mathematical Sciences, Shanghai Jiao Tong University, Shanghai, China;1. Department of Biochemistry and Biomedical Sciences and the Michael G. DeGroote Institute for Infectious Diseases Research, McMaster University, Hamilton, ON L8S 4L8, Canada |
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| Abstract: | We report for the first time the conformational analysis of dibenzo-18-crown-6, db18c6. The conformational search was carried out using the CONFLEX conformational search method of cyclic molecules. Energies were calculated for the low-lying predicted conformations at different levels of theory up to the G3MP2 level. At the G3MP2 level, the predicted ground state (GS) conformation was more stable than the experimental conformation by only 1.60 kcal/mol. Strong similarity was found between the GS structure and experimental conformations of db18c6 and 18-crown-6, 18c6. The GS and experimental conformations of db18c6 are non-planar. This allows db18c6 to exist in optically active enantiomers. Similar to 18c6, it was concluded that the db18c6 structure is stabilized by intramolecular hydrogen bond. We also performed the computations for the water and chloroform solution phase, where the same conformation was predicted as the GS conformation. |
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| Keywords: | Crown ethers Dibenzo-18-crown-6 Conformational analysis Structure of dibenzo-18-crown-6 CONFLEX conformational search G3MP2 |
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