Study of the Structure of (Carbamimidoylsulfanyl)Acetic (“Pseudothiohydantoic”) Acid by XRD and PM6 Methods

Russian Journal of Organic Chemistry 2013
V.S. Fundamenskis, S.M. Ramšs, V.A. Bruskovs, A.V. Smirnova, A.J. Janičevs, M.B. Fleišers, Sergejs Beļakovs

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.

DOI
10.1134/S1070428013050060
Hipersaite
http://link.springer.com/article/10.1134%2FS1070428013050060#

Fundamenskis, V., Ramšs, S., Bruskovs, V., Smirnova, A., Janičevs, A., Fleišers, M., Beļakovs, S. Study of the Structure of (Carbamimidoylsulfanyl)Acetic (“Pseudothiohydantoic”) Acid by XRD and PM6 Methods. Russian Journal of Organic Chemistry, 2013, Vol.49, Iss.5, 672.-677.lpp. e-ISSN 1608-3393. ISSN 1070-4280. Pieejams: doi:10.1134/S1070428013050060

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