| Publication Type |
Journal Article |
| Title |
Quaternization reaction of aromatic heterocyclic imines in methanol - A case of strong anti-reactivity selectivity principle with isoselective temperature |
| Authors |
AJI Alfaia ART Calado JC Reis |
| Groups |
MTFT |
| Journal |
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY |
| Year |
2000 |
| Month |
November |
| Volume |
|
| Number |
21 |
| Pages |
3627-3631 |
| Abstract |
Accurate second-order rate constants were measured at 5 degreesC intervals in the temperature range 20-60 degreesC for the Menshutkin reaction of 1-methylbenzimidazole, 2-amino-1-methylbenzimidazole and N,N-dimethylaniline with iodomethane and iodoethane in methanol. In every case a good linearity in the Eyring plots was observed. Values for the activation enthalpy and entropy are reported. Analysis in terms of Exner s redefinition of the reactivity-selectivity principle (RSP) identified the present reaction series as a case of strong anti-RSP for selectivity towards the substrate. This case is shown to represent an isoselective relationship with the isoselective temperature lower than the experimental temperatures (beta (is) = -52 degreesC). The isokinetic relationship does not hold in the reaction series with a fixed substrate. These findings suggest an early transition state in the Menshutkin reaction of polyfunctional aromatic imines. |
| DOI |
http://dx.doi.org/ |
| ISBN |
|
| Publisher |
|
| Book Title |
|
| ISSN |
1434-193X |
| EISSN |
|
| Conference Name |
|
| Bibtex ID |
ISI:000165165800015 |
| Observations |
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