at Google ScholarTitle data
Bringmann, Gerhard ; Vitt, Daniel ; Kraus, Jürgen ; Breuning, Matthias:
The ortho-Hydroxy-ortho'-Formyl Biaryl/Lactol Equilibrium : Quantumchemical Studies on Structure and Dynamics.
In: Tetrahedron.
Vol. 54
(1998)
Issue 36
.
- pp. 10691-10698.
ISSN 0040-4020
DOI: https://doi.org/10.1016/S0040-4020(98)00619-X
Abstract in another language
The equilibrium between the lactol-bridged biaryls 3 and the ring opened hydroxy aldehyde isomers 4 as well as their atropisomerization are investigated by quantumchemical calculations. The suitability of semiempirical and different modern ab initio methods is validated by comparison with experimentally observed equilibria and crystallographic data. It is shown that for the description of the equilibrium between 3 and 4 Hartree-Fock ab initio methods lead to a significant improvement compared with semiempirical methods. Furthermore, the consideration of solvent effects by using AM1-SM4, PM3-SM4 and PM3-SM3 gives satisfying results in the description of the equilibrium investigated.
Ab initio methods as well as semiempirical calculations give a good description of the atropisomerization behavior of helically twisted lactol-bridged biaryls, whereas ab initio methods are required for the calculation of the equilibrium between the hydroxy aldehydes 4 and their lactol-type isomers 3.
Further data
| Item Type: | Article in a journal |
|---|---|
| Refereed: | Yes |
| Institutions of the University: | Faculties Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry > Professor Organic Chemistry - Univ.-Prof. Dr. Matthias Breuning Faculties > Faculty of Biology, Chemistry and Earth Sciences Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry |
| Result of work at the UBT: | No |
| DDC Subjects: | 500 Science 500 Science > 540 Chemistry |
| Date Deposited: | 03 Jul 2017 12:23 |
| Last Modified: | 12 Jan 2022 13:48 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/38239 |