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Note | Regular issue | Vol 75, No. 6, 2008, pp.1457-1466
Published online, 15th February, 2008
DOI: 10.3987/COM-07-11305
Metalloreceptors Composed of Organopalladium Complexes Containing 5-Mercapto-3H-1,3,4-thiadiazolin-2-ones

Nam Sook Cho,* Sang Beom Kim, Min Hye Kim, Seong Gyun Park, Sung Kown Kang, Se Jin Lee, and Yeong-Joon Kim

*Department of Chemistry, Chungnam National University, Daejeon, 305-764, Korea

Abstract

Macrocyclic ligands containing two 5-mercapto-3H-1,3,4-thiadiazoline-2-one groups and one 1,3-benzenedimethanethiol group, which served to link the 2- and 5-positions of the heterocycle unit and chelate palladium ion, respectively, were synthesized by regiospecific S-alkylation of 5-ethoxy-3H-1,3,4-thiadiazoline-2-thione. The structures of the resulting metalloreceptors were established using 1H and 13C NMR, FTIR spectroscopy, MS spectrometry, and elemental analysis. The molecular recognition ability of the metalloreceptors was examined against DNA/RNA nucleobases and acetanilide. The complexa- tion strength of both compounds increased in the order acetanilide/uracil/thymine < adenine < cytosine.