Hydrogen bonding and steric effects on rotamerization in 3, 4-alkylenedioxy-, 3-alkoxy-and 3, 4-dialkoxy-2-thienyldi (tert-butyl) methanols: an NMR, IR and X-ray …

…, A Adenier, K Gao, F Maurel, J Vaissermann

Index: Lomas, John S.; Adenier, Alain; Gao, Kun; Maurel, Francois; Vaissermann, Jacqueline Journal of the Chemical Society, Perkin Transactions 2, 2002 , # 2 p. 216 - 224

Full Text: HTML

Citation Number: 1

Abstract

The equilibrium constant for the anti↔ syn rotamerization (anti: intramolecularly hydrogen- bonded hydroxy group; syn:“free” hydroxy group) of 3, 4-alkylenedioxy-, 3-alkoxy-and 3, 4- dialkoxy-2-thienyldi (tert-butyl) methanols depends on the 3, 4-alkylenedioxy or alkoxy group (s) and the solvent, hydrogen-bonding solvents such as DMSO and pyridine favouring the syn isomer. Equilibrium constants ([syn]/[anti]) in chloroform and benzene decrease in ...