Ionic cocrystals of molecular saccharin

Durga Prasad Karothu, Ilma Jahović, Gligor Jovanovski, Branko Kaitner, Pance Naumov

    Research output: Contribution to journalArticle

    Abstract

    Saccharin is a cyclic sulfimide whose sodium salt, commercially available under the trade name "Sweet'N Low", is one of the most commonly used artificial low-calorie sweeteners and is also the main sugar substitute in the diet of diabetics. Being an acid (pKa = 1.6), it is readily deprotonated in solution and affords solid ionic salts or coordination compounds with transition metals where its conjugate base (saccharinate ion) displays a wealth of coordination modes. Here we report the first two examples of ionic cocrystals of molecular saccharin where saccharin exists as a neutral species and an ion in the same crystal. With rubidium and cesium cations, saccharin forms isomorphous solid hemihydrate salts. When saccharin is supplied in excess to the reaction mixture, neutral saccharin molecules are stoichiometrically incorporated into both crystals and stable isomorphous ionic cocrystals are obtained. The formation of ionic cocrystals is unprecedented and adds a new aspect to the rich crystal chemistry of this artificial sweetener.

    Original languageEnglish (US)
    Pages (from-to)4338-4344
    Number of pages7
    JournalCrystEngComm
    Volume19
    Issue number30
    DOIs
    StatePublished - Jan 1 2017

    Fingerprint

    Saccharin
    Salts
    salts
    Sweetening Agents
    Sugar substitutes
    Crystal chemistry
    crystals
    diets
    Rubidium
    Crystals
    Trademarks
    Ions
    Cesium
    Nutrition
    rubidium
    sugars
    cesium
    Transition metals
    ions
    Positive ions

    ASJC Scopus subject areas

    • Chemistry(all)
    • Materials Science(all)
    • Condensed Matter Physics

    Cite this

    Karothu, D. P., Jahović, I., Jovanovski, G., Kaitner, B., & Naumov, P. (2017). Ionic cocrystals of molecular saccharin. CrystEngComm, 19(30), 4338-4344. https://doi.org/10.1039/c7ce00627f

    Ionic cocrystals of molecular saccharin. / Karothu, Durga Prasad; Jahović, Ilma; Jovanovski, Gligor; Kaitner, Branko; Naumov, Pance.

    In: CrystEngComm, Vol. 19, No. 30, 01.01.2017, p. 4338-4344.

    Research output: Contribution to journalArticle

    Karothu, DP, Jahović, I, Jovanovski, G, Kaitner, B & Naumov, P 2017, 'Ionic cocrystals of molecular saccharin', CrystEngComm, vol. 19, no. 30, pp. 4338-4344. https://doi.org/10.1039/c7ce00627f
    Karothu DP, Jahović I, Jovanovski G, Kaitner B, Naumov P. Ionic cocrystals of molecular saccharin. CrystEngComm. 2017 Jan 1;19(30):4338-4344. https://doi.org/10.1039/c7ce00627f
    Karothu, Durga Prasad ; Jahović, Ilma ; Jovanovski, Gligor ; Kaitner, Branko ; Naumov, Pance. / Ionic cocrystals of molecular saccharin. In: CrystEngComm. 2017 ; Vol. 19, No. 30. pp. 4338-4344.
    @article{244ae4053cb248f28e7e4749c556f898,
    title = "Ionic cocrystals of molecular saccharin",
    abstract = "Saccharin is a cyclic sulfimide whose sodium salt, commercially available under the trade name {"}Sweet'N Low{"}, is one of the most commonly used artificial low-calorie sweeteners and is also the main sugar substitute in the diet of diabetics. Being an acid (pKa = 1.6), it is readily deprotonated in solution and affords solid ionic salts or coordination compounds with transition metals where its conjugate base (saccharinate ion) displays a wealth of coordination modes. Here we report the first two examples of ionic cocrystals of molecular saccharin where saccharin exists as a neutral species and an ion in the same crystal. With rubidium and cesium cations, saccharin forms isomorphous solid hemihydrate salts. When saccharin is supplied in excess to the reaction mixture, neutral saccharin molecules are stoichiometrically incorporated into both crystals and stable isomorphous ionic cocrystals are obtained. The formation of ionic cocrystals is unprecedented and adds a new aspect to the rich crystal chemistry of this artificial sweetener.",
    author = "Karothu, {Durga Prasad} and Ilma Jahović and Gligor Jovanovski and Branko Kaitner and Pance Naumov",
    year = "2017",
    month = "1",
    day = "1",
    doi = "10.1039/c7ce00627f",
    language = "English (US)",
    volume = "19",
    pages = "4338--4344",
    journal = "CrystEngComm",
    issn = "1466-8033",
    publisher = "Royal Society of Chemistry",
    number = "30",

    }

    TY - JOUR

    T1 - Ionic cocrystals of molecular saccharin

    AU - Karothu, Durga Prasad

    AU - Jahović, Ilma

    AU - Jovanovski, Gligor

    AU - Kaitner, Branko

    AU - Naumov, Pance

    PY - 2017/1/1

    Y1 - 2017/1/1

    N2 - Saccharin is a cyclic sulfimide whose sodium salt, commercially available under the trade name "Sweet'N Low", is one of the most commonly used artificial low-calorie sweeteners and is also the main sugar substitute in the diet of diabetics. Being an acid (pKa = 1.6), it is readily deprotonated in solution and affords solid ionic salts or coordination compounds with transition metals where its conjugate base (saccharinate ion) displays a wealth of coordination modes. Here we report the first two examples of ionic cocrystals of molecular saccharin where saccharin exists as a neutral species and an ion in the same crystal. With rubidium and cesium cations, saccharin forms isomorphous solid hemihydrate salts. When saccharin is supplied in excess to the reaction mixture, neutral saccharin molecules are stoichiometrically incorporated into both crystals and stable isomorphous ionic cocrystals are obtained. The formation of ionic cocrystals is unprecedented and adds a new aspect to the rich crystal chemistry of this artificial sweetener.

    AB - Saccharin is a cyclic sulfimide whose sodium salt, commercially available under the trade name "Sweet'N Low", is one of the most commonly used artificial low-calorie sweeteners and is also the main sugar substitute in the diet of diabetics. Being an acid (pKa = 1.6), it is readily deprotonated in solution and affords solid ionic salts or coordination compounds with transition metals where its conjugate base (saccharinate ion) displays a wealth of coordination modes. Here we report the first two examples of ionic cocrystals of molecular saccharin where saccharin exists as a neutral species and an ion in the same crystal. With rubidium and cesium cations, saccharin forms isomorphous solid hemihydrate salts. When saccharin is supplied in excess to the reaction mixture, neutral saccharin molecules are stoichiometrically incorporated into both crystals and stable isomorphous ionic cocrystals are obtained. The formation of ionic cocrystals is unprecedented and adds a new aspect to the rich crystal chemistry of this artificial sweetener.

    UR - http://www.scopus.com/inward/record.url?scp=85026654882&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=85026654882&partnerID=8YFLogxK

    U2 - 10.1039/c7ce00627f

    DO - 10.1039/c7ce00627f

    M3 - Article

    VL - 19

    SP - 4338

    EP - 4344

    JO - CrystEngComm

    JF - CrystEngComm

    SN - 1466-8033

    IS - 30

    ER -