Correlation of Hammett Parameters (σ σ+) With 1H-NMRand 13C-NMR of Some 4-Aryl-1, 4-Dihydropyridines (Hantzsch-Esters)
✍ Scribed by R. A. Dommisse; J. A. Lepoivre; F. C. Alderweireldt
- Publisher
- Wiley (John Wiley & Sons)
- Year
- 2010
- Weight
- 168 KB
- Volume
- 86
- Category
- Article
- ISSN
- 0037-9646
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✦ Synopsis
Abstract
^1^H‐NMR and ^13^C‐NMR spectral data of 4‐aryl‐3, 5‐diethoxycarbonyl‐2, 6‐dimethyl‐1,4‐dihydropyridines (Hantzsch‐esters) are given. The chemical shift variations resulting from the different substituents are related to Hammett σ‐ and σ^+^‐constants.
The 1, 4‐dihydropyridines of the Hantzsch‐ester type have been of increasing interest for studies on their spectroscopic properties and their use as model compounds for the NAD/NADH coenzyme system. Recently a study of the U.V.‐ and I.R.‐spectra of 4‐aryl‐3, 5‐diethoxycarbonyl‐2, 6‐dimethyl‐1, 4‐dihydropyridines has been published (1). Mass spectral data of the same compounds and their N‐alkylated analogs are also available (2). Although ^1^H‐NMR played a very important role in the determination of the exact structure of several dihydropyridine derivatives, only a small amount of systematic investigation has been done. In this paper the influence of various aryl substituents on the ^1^H‐NMR and ^13^C‐NMR chemical shift values in the dihydropyridine moiety of the above mentioned compounds is studied.