Aromatic imine stereochemistry as studied by 13C and 1H NMR of 15N‐enriched materials
- 1 April 1980
- journal article
- research article
- Published by Wiley in Magnetic Resonance in Chemistry
- Vol. 13 (4) , 293-298
- https://doi.org/10.1002/mrc.1270130416
Abstract
A series of thirteen 15N‐enriched N‐aryl imines derived from benzaldehydes and acetophenones have been prepared and examined by 13C and 1H NMR. Preferred conformations of the C‐arvl and N‐aryl rings have been deduced from 13C chemical shifts and 13C‐15N couplings. Evidence for steric inhibition of resonance in O‐alkylated materials is presented. Relative signs of 1J(CN) and 2J(CCN) have been determined in some compounds. An E: Z interconversion barrier of 21.6 kcal mol−1 has been obtained from 1H NMR coalescence data.Keywords
This publication has 21 references indexed in Scilit:
- Characterization of coupling constants to nitrogen. Carbon‐13 chemical shifts and carbon–nitrogen coupling constants of substituted benzaldoximesMagnetic Resonance in Chemistry, 1979
- Carbon‐13 nuclear magnetic resonance of the azomethine group. II—(II.II) conjugation and twist anglesMagnetic Resonance in Chemistry, 1977
- Etude du Groupe Azomethine par RMN du Carbone‐13. Cétimines et Dibenzo[b, f] diazocines[1,4]Magnetic Resonance in Chemistry, 1977
- A study of 13C–15N couplings and revised 13C shieldings in 15N-enriched E-acetophenone oximesCanadian Journal of Chemistry, 1976
- Geometrical dependences of carbon-nitrogen coupling constants. OximesJournal of the American Chemical Society, 1974
- Mechanism of interconversion of (Z)-and (E)-ketiminesJournal of the American Chemical Society, 1972
- INDO Molecular Orbital Calculations of Nitrogen–Proton Spin–Spin Coupling Constants Over Two and Three Bonds. Effects of Lone-pair Orientation, of Dihedral Angles, and of ProtonationCanadian Journal of Chemistry, 1972
- The effect of solvent interactions and hydrogen bonding on 15N chemical shifts and 15NH coupling constantsJournal of Magnetic Resonance (1969), 1970
- Uncatalyzed syn-anti Isomerization of Imines, Oxime Ethers, and Haloimines1Journal of the American Chemical Society, 1966
- Antihistamin-Substanzen XLIX. p-Substituierte N-(α-Phenyläthyl)äthylendiamin-DerivateCollection of Czechoslovak Chemical Communications, 1962