Normal, Leveled, and Enhanced Steric Effects in Alkoxyamines Carrying a β-Phosphorylated Nitroxyl Fragment

The Journal of Organic Chemistry
Gérard AudranPaulin Nkolo

Abstract

The design of new R1R2NOR3 alkoxyamines for various applications relies on the accurate prediction of two kinetic parameters, the C-ON bond homolysis rate constant (kd) and its re-formation rate constant (kc). Relationships to describe the steric and polar effects of the R1R2NO fragment ruling kd have been developed. For all cyclic nitroxyl fragments, the steric effect is described as the sum of the bulkiness of the R1 and R2 groups (i.e., normal steric effect), while for the noncyclic nitroxyl fragment (except for one case), a leveled steric effect is assumed. In this work, we show that the normal steric effect also applies to noncyclic nitroxyl fragments and that for one case an enhanced steric effect is also observed, i.e., experimental kd >5-fold larger than the predicted value.

References

Aug 5, 2010·Angewandte Chemie·Birte SchulteLuisa De Cola
Mar 7, 2012·Journal of the American Chemical Society·Jing XuEmmanuel A Theodorakis
Dec 18, 2013·Organic & Biomolecular Chemistry·Gérard AudranEric Thiaudière
Feb 28, 2014·Chemical Reviews·Elena G Bagryanskaya, Sylvain R A Marque
Jun 18, 2014·Molecular Pharmaceutics·Damien MonceletPhilippe Mellet
May 27, 2015·Nature Communications·Raj Kumar RoyJean-François Lutz
Sep 12, 2015·Chemical Communications : Chem Comm·Raj Kumar RoyJean-François Lutz
Mar 18, 2016·Organic & Biomolecular Chemistry·Gérard AudranSylvain R A Marque

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Citations

Sep 28, 2017·Organic & Biomolecular Chemistry·Gérard AudranValérie Roubaud
Aug 28, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Thibaud ReyserGérard Audran
Nov 4, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sergey CherkasovElena Bagryanskaya
Nov 12, 2020·Accounts of Chemical Research·Gérard AudranPhilippe Mellet

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