Studies of some monocyclic and bicyclic arylacetonitriles
Copyright © 2011 John Wiley & Sons, Ltd.
| Veröffentlicht in: | Magnetic resonance in chemistry : MRC. - 1985. - 49(2011), 5 vom: 01. Mai, Seite 262-78 |
|---|---|
| 1. Verfasser: | |
| Weitere Verfasser: | |
| Format: | Online-Aufsatz |
| Sprache: | English |
| Veröffentlicht: |
2011
|
| Zugriff auf das übergeordnete Werk: | Magnetic resonance in chemistry : MRC |
| Schlagworte: | Letter Acetonitriles Bridged Bicyclo Compounds |
| Zusammenfassung: | Copyright © 2011 John Wiley & Sons, Ltd. The high-resolution (1)H, (13)C, (1)H-(1)H COSY and (1)H-(13)C COSY NMR spectra have been recorded in CDCl(3) for arylacetonitriles 1-12 and analyzed. The arylacetonitriles 3-7 exist in two isomeric forms E (methyl group is anti to cyano group) and Z (the methyl group is syn to cyano group) in solution. Normal chair conformation with equatorial orientations of phenyl rings at C-2 and C-6 for monocyclic nitriles 1 and 2, epimeric chair structure EC (axial configuration of methyl group at C-3) for both the E and Z isomers of arylacetonitrile derivatives (3-7) and a distorted boat form, B(3), for the N-acylacetonitrile derivatives (8-10) have been proposed based on NMR data. The bicyclic nitriles 11 and 12 exist in twin chair conformations in solution. DFT calculations and chemical shifts also support these conformations. Geometry optimizations for 1-12 were carried out according to density functional theory using B3LYP/6-31G(d,p) basis set and for 1 and 8 the theoretical geometrical parameters have been compared with those of single crystal measurements |
|---|---|
| Beschreibung: | Date Completed 05.08.2011 Date Revised 25.11.2016 published: Print-Electronic Citation Status MEDLINE |
| ISSN: | 1097-458X |
| DOI: | 10.1002/mrc.2734 |