Study of the structure of (carbamimidoylsulfanyl)acetic ('pseudothiohydantoic') acid by XRD and PM6 methods

Fundamenskii, V.; Ramsh, S.; Brouskov, V.; Smirnova, A.; Yanichev, A.; Fleisher, M.; Belyakov, S.
May 2013
Russian Journal of Organic Chemistry;May2013, Vol. 49 Issue 5, p672
Academic Journal
It was shown by the method of powder X-ray diffraction analysis that in the crystalline state the product of the reaction of thiourea with chloroacetic acid in water, (carbamimidoylsulfanyl)acetic acid, existed in the zwitter-ion tautomeric form. The structure consists of virtually planar infi nite layers normal to the c axis of the unit cell which are bound by van der Waals interactions. The layers are formed by infi nite rows elongated along the b axis of the unit cell consisting of materially planar zwitter-ionic molecules linked by strong bifurcated hydrogen bonds. The results of quantum-chemical calculations by PM6 method are in agreement with the XRD results: whereas an isolated molecule exists in nonzwitter-ionic tautomeric form, in the crystal only the zwitterionic tautomer is present.


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