Properties of thetert-butyl halide solvolysis transition states
Physical Chemistry Chemical Physics, ISSN: 1463-9076, Vol: 23, Issue: 5, Page: 3311-3320
2021
- 4Citations
- 9Captures
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Metrics Details
- Citations4
- Citation Indexes4
- CrossRef3
- Captures9
- Readers9
Article Description
We have obtained properties (or descriptors) of the transition states in the solvolysis oftert-butyl chloride, bromide and iodide. We show that all three transition states, in both protic and in aprotic solvents, are highly dipolar and are strong hydrogen bond acids and strong hydrogen bond bases, except for thetert-butyl iodide transition state in aprotic solvents, which has a rather low hydrogen bond acidity. Thus, the transition states are stabilized by solvents that are hydrogen bond bases (nucleophiles) and are hydrogen bond acids (electrophiles). We show also that the partition of the transition states between water and solvents is aided by both nucleophilic and electrophilic solvents and conclude that the rate of solvolysis of the three halides is increased by both nucleophilic and electrophilic solvents.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=85100851314&origin=inward; http://dx.doi.org/10.1039/d0cp05099g; http://www.ncbi.nlm.nih.gov/pubmed/33527930; https://xlink.rsc.org/?DOI=D0CP05099G; https://dx.doi.org/10.1039/d0cp05099g; https://pubs.rsc.org/en/content/articlelanding/2021/cp/d0cp05099g
Royal Society of Chemistry (RSC)
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