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http://dx.doi.org/10.5012/bkcs.2006.27.2.243

Mixed Intramolecular Hydrogen Bonding in Dihydroxythiophene-based Units and Boron and Technetium Chelation  

Ko, Sang-won (Department of Chemistry and Molecular Science (BK 21), Korea Advanced Institute of Science and Technology (KAIST))
Park, Sang-Hyun (Center for HANARO Application Research, Korea Atomic Energy Research Institute)
Gwon, Hui-Jeong (Center for HANARO Application Research, Korea Atomic Energy Research Institute)
Lee, Jun-seong (Department of Chemistry and Molecular Science (BK 21), Korea Advanced Institute of Science and Technology (KAIST))
Kim, Min-Jeong (Department of Chemistry and Molecular Science (BK 21), Korea Advanced Institute of Science and Technology (KAIST))
Kwak, Yeon-ju (Department of Chemistry and Molecular Science (BK 21), Korea Advanced Institute of Science and Technology (KAIST))
Do, Young-kyu (Department of Chemistry and Molecular Science (BK 21), Korea Advanced Institute of Science and Technology (KAIST))
Churchill, David G. (Department of Chemistry and Molecular Science (BK 21), Korea Advanced Institute of Science and Technology (KAIST))
Publication Information
Bulletin of the Korean Chemical Society / v.27, no.2, 2006 , pp. 243-250 More about this Journal
Abstract
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 $[N_{amide}-H{\cdot}{\cdot}{\cdot}O]$ $[O-H{\cdot}{\cdot}{\cdot}O_{amide}]$ and $[N_{amide}-H{\cdot}{\cdot}{\cdot}S]$. Boron chelation with 5, 6 and 7 through the use of $BF_3, \;B(OH)_3 \;or \;B(OMe)_3$ was probed by $^1H$, $^{11}B$, and $^{13}C$ NMR spectroscopy. Technetium (I) chelation with 5, 6 and 7 was also studied via HPLC elutions using $[^{99m}Tc(CO)_3(OH_2)_3]^+$.
Keywords
Dihydroxythiophene; Hydrogen bonding; Boron chelation; Technetium-99m helation; $^{99m}Tc$ tricarbonyl;
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