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Note | Regular issue | Vol 68, No. 4, 2006, pp.811-819
Published online, 10th March, 2006
DOI: 10.3987/COM-06-10672
Organopalladium Complexes 5-Amino-3H-1,3,4-thiadiazoline-2-thione as Metalloreceptor

Nam Sook Cho,* Mi Sun Park, Young Hoon Kim, Young-Ae Yu, Hyun Jung Kwon, and Yeong-Joon Kim

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

Abstract

Macrocycles containing two 5-amino-3H-1,3,4-thiadiazoline-2-thione 5 linking the 2- and 5-positions of the heterocycle unit and one 1,3-benzenedime- thanethiol were prepared via the regiospecific S-alkylation of 5-amino-3H-1,3,4-thiadiazoline-2-thione. The 1,3-benzenedimethanethiol sites chelated to palladium metal ion to afford an organopalladium metalloreceptor. The structures of the macrocycles and metalloreceptors were established using 1H and 13C NMR, IR, MS spectrometry, and elemental analysis. The molecular recognition of the metalloreceptors (5a and 5b) was examined for some DNA/RNA nucleobases and some amino acid methyl ester by 1H NMR spectrometry. In case of 5a, the complexation ability increased in the order pyrazine / uracil /acetanilide < adenine < cytosine < phenylalanine methyl ester / tyrosine methyl ester. With 5b, the complexation ability also increased in the same order as 5a pyrazine / uracil 5a.