ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Micelle Formation in Liquid Ammonia

View Author Information
IPOS, The Page Laboratories, Department of Chemical and Biological Sciences, The University of Huddersfield, Queensgate, Huddersfield, HD1 3DH, United Kingdom
Cite this: J. Org. Chem. 2015, 80, 14, 7033–7039
Publication Date (Web):June 15, 2015
https://doi.org/10.1021/acs.joc.5b00830
Copyright © 2015 American Chemical Society

    Article Views

    696

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    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.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    Data fit to other models for conductivity and data for micelle catalysis. The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.5b00830.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 5 publications.

    1. Gregory G. Warr, Rob Atkin. Solvophobicity and amphiphilic self-assembly in neoteric and nanostructured solvents. Current Opinion in Colloid & Interface Science 2020, 45 , 83-96. https://doi.org/10.1016/j.cocis.2019.12.009
    2. K. Kellett, B. M. Duggan, M. K. Gilson. Facile synthesis of a diverse library of mono-3-substituted β-cyclodextrin analogues. Supramolecular Chemistry 2019, 31 (4) , 251-259. https://doi.org/10.1080/10610278.2018.1562191
    3. Marie-Claire Dul, Bertrand Braibant, Sandrine Dourdain, Stéphane Pellet-Rostaing, Damien Bourgeois, Daniel Meyer. Perfluoroalkyl- vs alkyl substituted malonamides: Supramolecular effects and consequences for extraction of metals. Journal of Fluorine Chemistry 2017, 200 , 59-65. https://doi.org/10.1016/j.jfluchem.2017.06.001
    4. Kyounghee Shin, Gyeonghyeon Gong, Jonas Cuadrado, Serim Jeon, Mintae Seo, Hong Sung Choi, Jae Sung Hwang, Youngbok Lee, Alberto Fernandez‐Nieves, Jin Woong Kim. Structurally Stable Attractive Nanoscale Emulsions with Dipole–Dipole Interaction‐Driven Interdrop Percolation. Chemistry – A European Journal 2017, 23 (18) , 4292-4297. https://doi.org/10.1002/chem.201604722
    5. Joseph M. Griffin, John H. Atherton, Michael I. Page, Nicholas T. Powles. Lipase catalysed conversion of triglycerides to amides in liquid ammonia. Journal of Physical Organic Chemistry 2016, 29 (12) , 768-772. https://doi.org/10.1002/poc.3583

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect