Micelle Formation in Liquid Ammonia

Joseph M. Griffin, John H. Atherton, Michael I. Page

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)


Perfluorinated long chain alkyl amides aggregate in liquid ammonia with increasing concentration which reflects micelle-type formation based on changes in 19F NMR chemical shifts. The critical micelle concentrations (cmc) decrease with increasing chain length and give Kleven parameters A = 0.18 and B = 0.19. The micelles catalyze the ammonolysis of esters in liquid ammonia. The corresponding perfluorinated long chain alkyl carboxylates form ion pairs in liquid ammonia, but the equilibrium dissociation constants indicate favorable interactions between the chains in addition to the electrostatic forces. These perfluorinated carboxylates form micelles in aqueous solution, and their cmc's generate a Kleven B-value = 0.52 compared with 0.30 for the analogous alkyl carboxylates. The differences in hydrophobicity of CH2 and CF2 units in water and liquid ammonia are discussed, as is the possible relevance to life forms in liquid ammonia. © 2015 American Chemical Society.
Original languageEnglish
Pages (from-to)7033-7039
Number of pages7
JournalJournal of Organic Chemistry
Issue number14
Early online date30 Jun 2015
Publication statusPublished - 17 Jul 2015


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