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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 27, Number 2
BKCSDE 27(2)
February 20, 2006 

Mixed Intramolecular Hydrogen Bonding in Dihydroxythiophene-based Units and Boron and Technetium Chelation
Sangwon Ko, Sang Hyun Park, Hui Jeong Gwon, Junseong Lee, Min Jeong Kim, Yeonju Kwak, Youngkyu Do, David G. Churchill*
Dihydroxythiophene, Hydrogen bonding, Boron chelation, Technetium-99m chelation, 99mTc tricarbonyl
Three novel potential metal ion chelating units have been synthesized and characterized: 5-hexylcarbamoyl-3,4-dihydroxythiophene-2-carboxylic acid methyl ester (5), 3-benzyloxy-4-hydroxythiophene-2,5-dicarboxylic acid bis-hexylamide (6), and 3,4-dihydroxythiophene-2,5-dicarboxylic acid bis-hexylamide (7). The crystal structure of 6 was obtained and suggests the presence of three distinct intramolecular hydrogen bonds, namely [Namide-H…O] [O-H…Oamide] and [Namide-H…S]. Boron chelation with 5, 6 and 7 through the use of BF3, B(OH)3 or B(OMe)3 was probed by 1H, 11B, and 13C NMR spectroscopy. Technetium (I) chelation with 5, 6 and 7 was also studied via HPLC elutions using [99mTc(CO)3(OH2)3]+.
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