Are α-centered peptide radicals stabilized by a capto-dative effect?

Jochen J. Brocks, Frank M. Welle, Hans Dieter Beckhaus, Christoph Rüchardt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

The kinetics of the thermal C-C-cleavage reaction of the dimer of sarcosine anhydride 5 has been investigated between 295 and 333 °C in mesitylene. From the temperature dependence and from the release of strain on dissociation the cyclic α-peptide radical 6 was calculated to have a radical stabilization enthalpy (RSE) of -6.3 ± 1.3 kcal / mol thus indicating the absence of a synergistic capto-dative effect.

Original languageEnglish
Pages (from-to)7721-7724
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number44
DOIs
Publication statusPublished - 3 Nov 1997
Externally publishedYes

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