Why are sec-alkylperoxyl bimolecular self-reactions orders of magnitude faster than the analogous reactions of tert-alkylperoxyls? The unanticipated role of CH hydrogen bond donation-Reference-Cited by-同舟云学术

Why are sec-alkylperoxyl bimolecular self-reactions orders of magnitude faster than the analogous reactions of tert-alkylperoxyls? The unanticipated role of CH hydrogen bond donation

Published:2016 Issue:34 Volume:18 Page:23673-23679
ISSN:1463-9076
Container-title:Physical Chemistry Chemical Physics
language:en
Short-container-title:Phys. Chem. Chem. Phys.

Author:

Lee Richmond¹²³⁴⁵^ORCID,Gryn'ova Ganna¹²³⁴⁵,Ingold K. U.⁶⁷⁸,Coote Michelle L.¹²³⁴⁵^ORCID

Affiliation:

1. ARC Centre of Excellence for Electromaterials Science

2. Research School of Chemistry

3. Australian National University

4. Canberra ACT 2601

5. Australia

6. National Research Council

7. Ottawa

8. Canada

Abstract

Theory reveals that pri- and sec-alkylperoxyl bimolecular self-reactions are orders of magnitude faster than the analogous tert-alkylperoxyl reactions, because of the formation of 5-center cyclic CH⋯O hydrogen bonding.

Funder

Australian Research Council

Publisher

Royal Society of Chemistry (RSC)

Subject

Physical and Theoretical Chemistry,General Physics and Astronomy

Link

http://pubs.rsc.org/en/content/articlepdf/2016/CP/C6CP04670C

Reference55 articles.

1. J. A. Howard , in Peroxyl Radicals, ed. Z. B. Alfassi, Wiley, New York, 1997, pp. 283–334. This excellent review contains a host of rate and equilibrium constants for ROO˙ reactions, all properly cited. Therefore we will reference only publications that are particularly germane to our subject

2. Oxygen-18 Tracer Studies of Alkylperoxy Radicals. I. The Cumylperoxy Radical and Chain Termination in the Autoxidation of Cumene

3. Di-tert-butyl trioxide and di-tert-butyl tertoxide

4. The equilibrium between tertiary alkylperoxy-radicals and tetroxide molecules

5. Di-t-alkyl tetroxides

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