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| Content Provider | Springer Nature Link |
|---|---|
| Author | NEMATOLLAHI, DAVOOD GHASEMI, FATEMEH KHAZALPOUR, SADEGH VARMAGHANI, FAHIMEH |
| Copyright Year | 2016 |
| Abstract | Oxidative coupling reaction of some catechols has been studied by cyclic voltammetry at the glassy carbon electrode in different experimental conditions. The electrogenerated o-banzoquinone participates in a coupling reaction with anionic and dianionic forms of catechol. Based on EC mechanism, the observed homogenous rate constants of the coupling reaction of catechols were estimated by analyzing the cyclic voltammetric responses using the simulation software DIGIELCH. This paper deals with reaction of o-benzoquinones derived by the oxidation of catechol (CAT), 3-methylcatechol (3-MC), 3-methoxycatechol (3-MOC) and 3,4-dihydroxybenzoic acid (3,4-DHBA) with cycloheptylamine (a primary aliphatic amine) and aniline (a primary aromatic amine) as nucleophiles to gain mechanistic insight. The outcome indicates participation of o-benzoquinone in the Michael addition reaction with the studied primary amines. The best fit of the experimental and simulated results was obtained for ECE mechanism. The calculated/estimated homogeneous rate constants (k $_{obs}$) for Michael addition reaction were found to vary in the order CAT >3-MC >3-MOC >3,4-DHBA and CAT >3,4-DHBA >3-MC >3-MOC for cycloheptylamine and aniline, respectively. These data are in agreement with the trend of electronic properties (electron-donating/-withdrawing) of the substitutions on the catechol ring. Graphical Abstract Oxidative coupling reaction of some catechols has been studied in the presence of cycloheptylamine and aniline as nucleophiles to gain mechanistic insight. |
| Starting Page | 1887 |
| Ending Page | 1894 |
| Page Count | 8 |
| File Format | |
| ISSN | 09743626 |
| Journal | Journal of Chemical Sciences |
| Volume Number | 128 |
| Issue Number | 12 |
| e-ISSN | 09737103 |
| Language | English |
| Publisher | Springer India |
| Publisher Date | 2016-11-04 |
| Publisher Institution | Indian Academy of Sciences |
| Publisher Place | New Delhi |
| Access Restriction | One Nation One Subscription (ONOS) |
| Subject Keyword | Catechol cyclic voltammetry cycloheptylamine aniline coupling reaction digital simulation. Chemistry/Food Science |
| Content Type | Text |
| Resource Type | Article |
| Subject | Chemistry |
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