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Ab initio and density functional studies of cooperative hydrogen bonding in calix[4]-and calix[6]arenes
| Content Provider | Paperity |
|---|---|
| Author | Novikov, A. N. Bacherikov, V. A. Shapiro, Yu E. Gren, A. I. |
| Abstract | The cone conformation of C 4 symmetry is shown by the Hartree-Fock method (3-21G basis) to be the predominant conformer of calix[4]arene; the compressed cone of C 2 symmetry is the major conformer of calix[6]arene. Using quantum chemical methods we calculated hydrogen bond cleavage energies for calix[4]-(ab initio and density functional methods) and calix[6]arene (ab initio), and also for the complex of calix[4]arene with carbon disulfide. These energies along with structural data point to the cooperative effect of hydrogen bonds. The results of these studies provided an explanation to the greater conformational lability of calix[6]arene compared with calix[4]arene molecules. It is also predicted that the nucleophilic substitution reaction involving calix[6]arene in the presence of weak bases and in aprotic solvents, as well as in the gas phase, will occur via diastereomeric transition states. |
| Starting Page | 1003 |
| Ending Page | 1015 |
| File Format | HTM / HTML |
| ISSN | 00224766 |
| DOI | 10.1007/s10947-006-0419-0 |
| Issue Number | 6 |
| Journal | Journal of Structural Chemistry |
| Volume Number | 47 |
| e-ISSN | 15738779 |
| Language | English |
| Publisher | Pleiades Publishing |
| Publisher Date | 2006-11-01 |
| Access Restriction | Open |
| Subject Keyword | Ab initio and density functional methods Cooperative effect Calix[4]arene Calix[6]arene Compressed cone conformer Hydrogen bond |
| Content Type | Text |
| Resource Type | Article |
| Subject | Materials Chemistry Physical and Theoretical Chemistry Inorganic Chemistry |
