Micelle Formation in Liquid Ammonia

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

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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
JournalJournal of Organic Chemistry
Volume80
Issue number14
DOIs
Publication statusPublished - 17 Jul 2015

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Micelles
Ammonia
Liquids
Electrostatic force
Critical micelle concentration
Chemical shift
Hydrophobicity
Chain length
Amides
Esters
Nuclear magnetic resonance
Ions
Water

Cite this

Griffin, J. M., Atherton, J. H., & Page, M. I. (2015). Micelle Formation in Liquid Ammonia. Journal of Organic Chemistry, 80(14), 7033-7039. https://doi.org/10.1021/acs.joc.5b00830
Griffin, Joseph M. ; Atherton, John H. ; Page, Michael I. / Micelle Formation in Liquid Ammonia. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 14. pp. 7033-7039.
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Griffin, JM, Atherton, JH & Page, MI 2015, 'Micelle Formation in Liquid Ammonia', Journal of Organic Chemistry, vol. 80, no. 14, pp. 7033-7039. https://doi.org/10.1021/acs.joc.5b00830

Micelle Formation in Liquid Ammonia. / Griffin, Joseph M.; Atherton, John H.; Page, Michael I.

In: Journal of Organic Chemistry, Vol. 80, No. 14, 17.07.2015, p. 7033-7039.

Research output: Contribution to journalArticle

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T1 - Micelle Formation in Liquid Ammonia

AU - Griffin, Joseph M.

AU - Atherton, John H.

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PY - 2015/7/17

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N2 - 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.

AB - 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.

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JF - Journal of Organic Chemistry

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Griffin JM, Atherton JH, Page MI. Micelle Formation in Liquid Ammonia. Journal of Organic Chemistry. 2015 Jul 17;80(14):7033-7039. https://doi.org/10.1021/acs.joc.5b00830