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Issue 30, 2017
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Ionic cocrystals of molecular saccharin

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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.

Graphical abstract: Ionic cocrystals of molecular saccharin

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Article information

02 Apr 2017
15 Jun 2017
First published
16 Jun 2017

CrystEngComm, 2017,19, 4338-4344
Article type

Ionic cocrystals of molecular saccharin

D. P. Karothu, I. Jahović, G. Jovanovski, B. Kaitner and P. Naumov, CrystEngComm, 2017, 19, 4338
DOI: 10.1039/C7CE00627F

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