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Note | Regular issue | Vol 63, No. 12, 2004, pp.2827-2836
Published online, 8th October, 2004
DOI: 10.3987/COM-04-10201
Organopalladium Complex Containing 5-Amino-3H-1,3,4-thiadiazolin-2-ones as Metalloreceptor for DNA/RNA Nucleobases

Nam Sook Cho,* Chun Ho Lee, Yeong-Joon Kim, Jae Soo Choi, and Sung Kwon Kang

*Department of Chemistry, College of Natural Sciences, Chungnam National University, Taejon 305-764, Korea

Abstract

Macrocycles containing two 5-amino-3H-1,3,4-thiadiazolin-2-ones linking the 3- and 5-positions of the heterocycle unit and one 1,3-benzenedimethanethiol were prepared via the regiospecific N-alkylation of 5-amino-3H-1,3,4-thiadiazolin-2-one. The 1,3-benzenedimethanethiol sites chelated to palladium metal ion to give an organopalladium metalloreceptor. The structures of the macrocycle and metalloreceptor were established using 1H and 13C NMR, IR, and MS spectrometry. The molecular recognition of the metalloreceptor (5) was examined for some DNA/RNA nucleobases using 1H NMR spectrometry. The complexation ability increased in the order uracil/thymine < adenine < cytosine/imidazole.