Isotope effects in nucleophilic substitution reactions X. The effect of changing the nucleophilic atom on ion-pairing in an SN2 reaction
| العنوان: | Isotope effects in nucleophilic substitution reactions X. The effect of changing the nucleophilic atom on ion-pairing in an SN2 reaction |
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| المؤلفون: | Yao-ren Fang, Kenneth Charles Westaway, Zhu-Gen Lai |
| المصدر: | Canadian Journal of Chemistry. 76:758-764 |
| بيانات النشر: | Canadian Science Publishing, 1998. |
| سنة النشر: | 1998 |
| مصطلحات موضوعية: | Organic Chemistry, chemistry.chemical_element, General Chemistry, Photochemistry, Sulfur, Catalysis, Ion, chemistry, Nucleophile, Kinetic isotope effect, Atom, Nucleophilic substitution, SN2 reaction, Alkaline hydrolysis |
| الوصف: | The effect of ion-pairing in an SN2 reaction is very different when the nucleophilic atom is changed from sulfur to oxygen, i.e., changing the nucleophile from thiophenoxide ion to phenoxide ion. When the nucleophile is sodium thiophenoxide, ion-pairing markedly alters the secondary α -deuterium kinetic isotope effect (transition state structure) and the substituent effect found by changing the para substituent on the nucleophile. When the nucleophile is sodium phenoxide, ion-pairing does not significantly affect the secondary α -deuterium or the chlorine leaving group kinetic isotope effects (transition state structure) or the substituent effects found by changing a para substituent on the nucleophile or the substrate. The different effects of ion-pairing may occur because the electron density on the hard oxygen atom of the sodium phenoxide is not affected significantly by ion-pairing.Key words: nucleophilic substitution, SN2, kinetic isotope effect, transition state, substituent effects, ion-pair. |
| تدمد: | 1480-3291 0008-4042 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::94962fb48f7898303ca69445d69f9eaf https://doi.org/10.1139/v98-056 |
| حقوق: | CLOSED |
| رقم الأكسشن: | edsair.doi...........94962fb48f7898303ca69445d69f9eaf |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 14803291 00084042 |
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