Unusual deuterium isotope effects in 13C NMR spectra of trans-stilbene
✍ Scribed by Ziatko Meić; Dražen Vikić-topić; Hans Güsten
- Publisher
- John Wiley and Sons
- Year
- 1984
- Tongue
- English
- Weight
- 823 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0749-1581
No coin nor oath required. For personal study only.
✦ Synopsis
A detailed analysis of the -C NMR spectra of trans-stilbene and ten deuteriated trans-stilbenes has been undertaken. Some unusual deuterium isotope effects on carbon-hydrogen spin-spin coupling constants could not be explained by the ordinary primary and secondary isotope effects. The positive and negative changes of "J(CH) were interpreted in terms of a steric effect, the vibrational influence of the C-D bond and the para-effect induced by deuterium. In this respect, deuterium behaves as a real substituent with electronic properties different from those of hydrogen. The deuterium isotope effects on -C NMR chemical shifts and carbon-deuterium coupling constants have also been determined.
📜 SIMILAR VOLUMES
Over 100 isotope effects on "C chemical shifts were determined in a series of deuteriated cis-stilbene isotopomers. The magnitude and sign of these effects depend on the position and the number of deuterium atoms in the molecule. The variations in two-and three-bond effects were rationalized by ste
In this and subsequent papers the deuterium isotope effect is defined as h(D,H)=S(D)-h(H) following the convention used in referencing chemical shifts [ 101.
Exchange of amide protons with deuterium results in changes of 13 C chemical shifts for carbon atoms near the site of substitution (CH{N and N{C|O). There is a measurable decrease in the isotopic shifts of CH{N for cycloalkylacetamides as ring size increases from 3 to 8 and for lactams as ring size
The temperature dependence of the deuterium isotope effect on the t3c NMR signals for various positions in the phenyl ring of 2-(N,N-diethylaminomethyl) tetrachlorophenol was studied in the moderately polar solvent CH2C12. The critical temperature, T~ = 245 K, corresponds to the compensation of oppo
Deuterium-induced isotope effects on 13C chemical shifts were measured in a series of benzene derivatives, viz. toluene, benzoic acid and benzophenone. The effects over two, three and four bonds reflect a dependence on the transmission pathway and the nature of the side-chain. Steric and inductive i