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Charge transfer complexes of some N-methylated thiohydantoins with molecular iodine

✍ Scribed by Franco Cristiani; Francesco A. Devillanova; Angelo Diaz; Francesco Isaia; Gaetano Verani

Publisher: John Wiley and Sons
Year: 1990
Tongue: English
Weight: 357 KB
Volume: 1
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520010504

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✦ Synopsis

Using a series o f N-methylated thiohydantoins as substrates, the donor properties o f the sulfur atom are measured by determining the stability constants ( K ) of their adducts with molecular iodine. The K's have been determined by recording the UV-visible spectra of several CH2C12 solutions with different amounts of the reagents. The experimental data fit the 1 : 1 adduct model for a11 the compounds. The K values, compared with those previously found for the unsubstituted hydantoins and with those obtained for 5-methyl-2thiohydantoin, show that the hydrogen-bonding interaction between the N H hydrogen and the S-bonded iodine plays an important role in determining the stability of' the adducl.

The K values obtained for several pentaatomic rings, all contuining the thioureido group -HN--C(=S)-NH-, are discussed on the basis of the influence of the substituents at C-4 and C-5 on the donor properties of the sulfur atom.

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