Muchall, Heidi M. and Werstiuk, Nick H (1998) A computational study on the sources of deuterium secondary kinetic isotope effects in carbocation-forming reactions. Canadian Journal of Chemistry, 76 (12). pp. 1926-1930. ISSN 0008-4042
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Official URL: http://dx.doi.org/10.1139/cjc-76-12-1926
Abstract
Calculations at the HF-DFT hybrid Becke3LYP level of theory have been undertaken on protonated 2-exo- and 2-endo-norbornanols as model substrates for 2-exo- and 2-endo-norbornyl brosylates to explore the source of the experimentally determined deuterium secondary kinetic isotope effects (KIEs). Calculations on protonated alcohols as models reproduce the "normal" behaviour of 2-endo substrate 5. The observed endo g-KIE in the 7-unsubstituted 2-exo system 4 is shown to arise from internal return, while those in the 7-chloro substituted 2-exo substrates 1 and 2 can be explained with competing 1,3 (6,2)-elimination
| Divisions: | Concordia University > Faculty of Arts and Science > Chemistry and Biochemistry |
|---|---|
| Item Type: | Article |
| Refereed: | Yes |
| Authors: | Muchall, Heidi M. and Werstiuk, Nick H |
| Journal or Publication: | Canadian Journal of Chemistry |
| Date: | December 1998 |
| Funders: |
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| Keywords: | deuterium secondary kinetic isotope effects, 2-norbornyl cation, Becke3LYP |
| ID Code: | 6767 |
| Deposited By: | DANIELLE DENNIE |
| Deposited On: | 12 Jul 2010 16:56 |
| Last Modified: | 08 Dec 2010 18:08 |
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