An x-ray study of 2-imino-4-oxo-l,3-thiazolidine and its hydrochloride

Abstract

2-Imino-4-oxo-l,3-thiazolidine, (L), is prepared 1 by the condensation of monochloroacetic acid with thiourea and subsequent hydrolysis of the product with sodium acetate. 2-Imino-4-oxo-l,3-thiazolidine hydrochloride, (LHC1), is prepared by treating L with 6N HCl. Very good colourless needle-shaped crystals of L and prismatic crystals of are obtained by slow evaporation from the respective aqueous solutions.The infrared spectra of the compounds indicate that a strong absorption at 3 225 cm -1 ascribed to exocyclic NH stretching frequency in L, has shifted to lower region (around 3100 cm -1 ) in LHC1. This suggests that in LHC1 the exocyclic -NH group is protonated.A weak intensity band observed at 3 400 cm -1 with a strong and broad band at 3000 cm -1 in L and LHC1 is due to cyclic NH stretching frequency. The appearance of NH stretching frequency, at lower region is attributed to the strong intermolecular hydrogen bonding present in the compounds.Single-crystal rotation and Weissenberg photographs were taken using CuKot radiation, down a axis for L and down a and c axes for LHC1. The crystal data for both the compounds are given in Table 1. LHC1, and (L) (LHC1)

The molecular and crystal structure of 2-imino-4-oxo-l,3-thiazolidine hydrochloride

“…crystal data (ANANTHAMURTHY, UDUPA and MURTHY, 1973) are given in Table 1. The structural formulae of the compound is…”