The search result changed since you submitted your search request. Documents might be displayed in a different sort order.
  • search hit 3 of 3
Back to Result List

Synthesis and NMR spectroscopic conformational analysis of esters of 4-hydroxy-cyclohexanone-the more polar the molecule the more stable the axial conformer

  • The esters of 4-hydroxy-cyclohexanone and a series of carboxylic acids R-COOH with R of different electronic and steric influence (R=Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, sec-Bu, t-Bu, CF3, CH2Cl, CHCl2, CCl3, CH2Br, CHBr2, and CBr3) were synthesized and the conformational equilibria studied by H-1 and C-13 NMR spectroscopy at 103 K and at 295 K, respectively. The geometry of optimized structures of the axial 'equatorial chair conformers was computed at the ab initio MO and DFT levels of theory. Only one preferred conformation was obtained for the axial and the equatorial conformer as well. When comparing the conformational equilibria of the cyclohexanone esters with those of the corresponding cyclohexyl esters a certain polarity contribution of the cyclohexanone framework was revealed, which is independent of the substituent effects and increases the stability of the axial conformers by a constant amount.

Export metadata

Additional Services

Search Google Scholar Statistics
Metadaten
Author details:Erich KleinpeterORCiDGND, Matthias HeydenreichORCiD, Andreas KochORCiDGND, Torsten LinkerORCiDGND
DOI:https://doi.org/10.1016/j.tet.2012.01.022
ISSN:0040-4020
Title of parent work (English):Tetrahedron
Publisher:Elsevier
Place of publishing:Oxford
Publication type:Article
Language:English
Year of first publication:2012
Publication year:2012
Release date:2017/03/26
Tag:4-Substituted cyclohexanones; ALTONA equation; Conformational analysis; Dynamic NMR; Quantum chemical calculations; Simulation of H-1 NMR spectra
Volume:68
Issue:10
Number of pages:11
First page:2363
Last Page:2373
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer review:Referiert
Accept ✔
This website uses technically necessary session cookies. By continuing to use the website, you agree to this. You can find our privacy policy here.