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

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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.
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