Kiefl, C. and Zinner, H. and Burgemeister, T. and Mannschreck, Albrecht (1996) Axially chiral 2-(dialkylamino)benzamides. Barriers to rotations, determined by NMR and by racemization (neighboring rotor substituents on arene systems .3.). RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 115 (2). pp. 125-132. ISSN 0165-0513
Full text not available from this repository.Abstract
The title compounds (Scheme 1, Y = NMe(2)) were investigated by variable-temperature NMR and/or by racemization of enantiomers enriched by liquid chromatography on microcrystalline triacetylcellulose. For several reasons, a dialkylamino and a dimethylcarbamoyl group were used, for the first time, as neighboring rotor substituents on a benzene ring. Barriers to rotations about their aryl-nitrogen and/or aryl-carbon bonds were determined and assigned (Table I). Correlated or uncorrelated motions of these groups are possible for amides 11 and 19 bearing in their 3-positions tert-butyl substituents which hinder the aryl-nitrogen rotation. Uncorrelated rotations have been found for amide 15 (Figure 2) and thioamide 8 which have the less voluminous bromine atom in their 3-position.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | LIQUID-CHROMATOGRAPHY; CHIROPTICAL DETECTION; CIRCULAR-DICHROISM; ENANTIOMERS; SPECTRA; enantiomers; correlated and uncorrelated motions; liquid chromatography on triacetylcellulose; thiobenzamides |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Nov 2023 09:57 |
| Last Modified: | 14 Nov 2023 09:57 |
| URI: | https://pred.uni-regensburg.de/id/eprint/51979 |
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