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Publication details

Document type
Journal articles

Document subtype
Full paper

Title
Properties of the tert-butyl halide solvolysis transition states

Participants in the publication
Michael H. Abraham (Author)
Filomena Martins (Author)
Dep. Química e Bioquímica
CQE-Ciências - Centro de Química Estrutural-Ciências
Ruben Elvas-Leitão (Author)
CQE-Ciências - Centro de Química Estrutural-Ciências
Luís Moreira (Author)

Scope
International

Refereeing
Yes

Summary
We have obtained properties (or descriptors) of the transition states in the solvolysis of tert-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 the tert-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.

Date of Submisson/Request
2020-09-27
Date of Acceptance
2021-01-25
Date of Publication
2021

Institution
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA

Where published
Physical Chemistry Chemical Physics

Publication Identifiers

Publisher
Royal Society of Chemistry (RSC)

Volume
23
Number
5

Number of pages
9
Starting page
3311
Last page
3320

Document Identifiers
DOI - https://doi.org/10.1039/d0cp05099g
URL - http://dx.doi.org/10.1039/d0cp05099g

Rankings
Google Metrics (2020) - 99 - Chemical & Material Sciences (general)
SCIMAGO Q1 (2019) - 1.143 - Physical and Theoretical Chemistry
Web Of Science Q2 (2019) - 3.430 - Physical Chemistry
Web Of Science Q1 (2019) - 3.430 - Physics, Atomic, Molecular & Chemical

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APA
Michael H. Abraham, Filomena Martins, Ruben Elvas-Leitão, Luís Moreira, (2021). Properties of the tert-butyl halide solvolysis transition states. Physical Chemistry Chemical Physics, 23, 3311-3320. http://dx.doi.org/10.1039/d0cp05099g

IEEE
Michael H. Abraham, Filomena Martins, Ruben Elvas-Leitão, Luís Moreira, "Properties of the tert-butyl halide solvolysis transition states" in Physical Chemistry Chemical Physics, vol. 23, pp. 3311-3320, 2021. 10.1039/d0cp05099g

BIBTEX
@article{50016, author = {Michael H. Abraham and Filomena Martins and Ruben Elvas-Leitão and Luís Moreira}, title = {Properties of the tert-butyl halide solvolysis transition states}, journal = {Physical Chemistry Chemical Physics}, year = 2021, pages = {3311-3320}, volume = 23 }