Synthesis and stacked conformations of symmetrical and unsymmetrical oligo-ureas of metaphenylenediamine

Jonathan Clayden*, Loïc Lemiègre, Madeleine Helliwell

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

29 Citations (Scopus)

Abstract

The addition of substituted anilines to nitro-substituted isocyanates followed by reduction generates new aniline-substituted ureas, which can be further extended in a one- or two-directional iterative manner to form oligomeric ureas based on a m-phenylenediamine monomer. Oligo-ureas with up to eight urea linkages are reported. Fully N-substituted oligo-ureas are crystalline, and the X-ray crystal structures display ring-stacked conformations. 1H NMR studies indicate that the stacked conformation persists in solution.

Original languageEnglish
Pages (from-to)2302-2308
Number of pages7
JournalJournal of Organic Chemistry
Volume72
Issue number7
Early online date8 Mar 2007
DOIs
Publication statusPublished - 30 Mar 2007

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