Study of Kinetics, Equilibrium and the Influence of Steric Effects on Proton-Transfer in the Reactions of 2, 2, 4- and 2, 6- Substituted Anilines with 2-Phenoxy-3,5-dinitropyridine in DMSO
Kinetic and equilibrium results for the reactions of 2-phenoxy-3,5-dinitropyridine (1), with a series of 2, 2, 4- and 2, 6- substituted anilines (2a-f), in the presence of DABCO in DMSO are reported. The reactions yield the 2-anilino derivatives (5), without the accumulation of intermediates. Kinet...
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| Format: | Article |
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Wiley
2010-01-01
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| Series: | E-Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2010/721387 |
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| author | Basim H. Asghar |
| author_facet | Basim H. Asghar |
| author_sort | Basim H. Asghar |
| collection | DOAJ |
| description | Kinetic and equilibrium results for the reactions of 2-phenoxy-3,5-dinitropyridine (1), with a series of 2, 2, 4- and 2, 6- substituted anilines (2a-f), in the presence of DABCO in DMSO are reported. The reactions yield the 2-anilino derivatives (5), without the accumulation of intermediates. Kinetics studies are compatible with a two-step mechanism involving initial nucleophilic attack by amine at the ring carbon substituted by phenoxy group followed by either base-catalyzed or uncatalyzed conversion to the product. The base-catalyzed pathway is likely to involve rate-limiting proton-transfer from the zwitterionic intermediate to base. This work indicates a steric effect to proton transfer in reactions involving 2, 6-disubstituted anilines. The results were compared with those for reactions of 1, 3, 5-trinitrobenzene with anilines. |
| format | Article |
| id | doaj-art-650a01f80b2c4b22b164aa912931a91e |
| institution | DOAJ |
| issn | 0973-4945 2090-9810 |
| language | English |
| publishDate | 2010-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | E-Journal of Chemistry |
| spelling | doaj-art-650a01f80b2c4b22b164aa912931a91e2025-08-20T03:18:14ZengWileyE-Journal of Chemistry0973-49452090-98102010-01-017125325910.1155/2010/721387Study of Kinetics, Equilibrium and the Influence of Steric Effects on Proton-Transfer in the Reactions of 2, 2, 4- and 2, 6- Substituted Anilines with 2-Phenoxy-3,5-dinitropyridine in DMSOBasim H. Asghar0Chemistry Department, Faculty of Applied Sciences, Umm Al-Qura University, P.O. Box: 9569, Makkah, Saudi ArabiaKinetic and equilibrium results for the reactions of 2-phenoxy-3,5-dinitropyridine (1), with a series of 2, 2, 4- and 2, 6- substituted anilines (2a-f), in the presence of DABCO in DMSO are reported. The reactions yield the 2-anilino derivatives (5), without the accumulation of intermediates. Kinetics studies are compatible with a two-step mechanism involving initial nucleophilic attack by amine at the ring carbon substituted by phenoxy group followed by either base-catalyzed or uncatalyzed conversion to the product. The base-catalyzed pathway is likely to involve rate-limiting proton-transfer from the zwitterionic intermediate to base. This work indicates a steric effect to proton transfer in reactions involving 2, 6-disubstituted anilines. The results were compared with those for reactions of 1, 3, 5-trinitrobenzene with anilines.http://dx.doi.org/10.1155/2010/721387 |
| spellingShingle | Basim H. Asghar Study of Kinetics, Equilibrium and the Influence of Steric Effects on Proton-Transfer in the Reactions of 2, 2, 4- and 2, 6- Substituted Anilines with 2-Phenoxy-3,5-dinitropyridine in DMSO E-Journal of Chemistry |
| title | Study of Kinetics, Equilibrium and the Influence of Steric Effects on Proton-Transfer in the Reactions of 2, 2, 4- and 2, 6- Substituted Anilines with 2-Phenoxy-3,5-dinitropyridine in DMSO |
| title_full | Study of Kinetics, Equilibrium and the Influence of Steric Effects on Proton-Transfer in the Reactions of 2, 2, 4- and 2, 6- Substituted Anilines with 2-Phenoxy-3,5-dinitropyridine in DMSO |
| title_fullStr | Study of Kinetics, Equilibrium and the Influence of Steric Effects on Proton-Transfer in the Reactions of 2, 2, 4- and 2, 6- Substituted Anilines with 2-Phenoxy-3,5-dinitropyridine in DMSO |
| title_full_unstemmed | Study of Kinetics, Equilibrium and the Influence of Steric Effects on Proton-Transfer in the Reactions of 2, 2, 4- and 2, 6- Substituted Anilines with 2-Phenoxy-3,5-dinitropyridine in DMSO |
| title_short | Study of Kinetics, Equilibrium and the Influence of Steric Effects on Proton-Transfer in the Reactions of 2, 2, 4- and 2, 6- Substituted Anilines with 2-Phenoxy-3,5-dinitropyridine in DMSO |
| title_sort | study of kinetics equilibrium and the influence of steric effects on proton transfer in the reactions of 2 2 4 and 2 6 substituted anilines with 2 phenoxy 3 5 dinitropyridine in dmso |
| url | http://dx.doi.org/10.1155/2010/721387 |
| work_keys_str_mv | AT basimhasghar studyofkineticsequilibriumandtheinfluenceofstericeffectsonprotontransferinthereactionsof224and26substitutedanilineswith2phenoxy35dinitropyridineindmso |