Water-soluble triazabutadienes that release diazonium species upon protonation under physiologically relevant conditions

Flora W. Kimani, John C Jewett

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

Triazabutadienes are an understudied structural motif that have remarkable reactivity once rendered water-soluble. It is shown that these molecules readily release diazonium species in a pH-dependent manner in a series of buffer solutions with pH ranges similar to those found in cells. Upon further development, we expect that this process will be well suited to cargo-release strategies and organelle-specific bioconjugation reactions. These compounds offer one of the mildest ways of generating diazonium species in aqueous solutions.

Original languageEnglish (US)
Pages (from-to)4051-4054
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number13
DOIs
Publication statusPublished - Mar 23 2015

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Keywords

  • diazonium salts
  • kinetics
  • protonation
  • triazabutadienes

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

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