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Micelle Formation in Liquid Ammonia

Griffin, Joseph M., Atherton, John H. and Page, Michael I. (2015) Micelle Formation in Liquid Ammonia. The Journal of Organic Chemistry, 80 (14). pp. 7033-7039. ISSN 0022-3263

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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 Bvalue
= 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.

Item Type: Article
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
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Depositing User: Elizabeth Boulton
Date Deposited: 30 Jul 2015 08:36
Last Modified: 04 Sep 2015 22:12


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