Complexation thermodynamics of cucurbit[6]uril with aliphatic alcohols, amines, and diamines
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- Title
- Complexation thermodynamics of cucurbit[6]uril with aliphatic alcohols, amines, and diamines
- Authors
- Rekharsky, MV; Ko, YH; Selvapalam, N; Kim, K; Inoue, Y
- Date Issued
- 2007-01
- Publisher
- TAYLOR & FRANCIS LTD
- Abstract
- Using the isothermal calorimetric titration technique, we determined the stability constants (K), reaction enthalpy (Delta H degrees), and entropy (Delta H degrees) for complexation of cucurbit[ 6] uril (CB[ 6]) with a series of aliphatic alcohols, monoand diamines, as well as spermidine and spermine, in aqueous solutions of alkali metal chlorides. The K for spermine reached 5.4 x 10(10) M-1 in 0.2M LiCl, which is the largest amongst the values reported for CB[ 6]. Propylamine forms the strongest 1: 1 complex with CB[6] (K = 21000 M-1) in 0.1 M Na acetate buffer, which is driven exclusively by entropy. A comparison of K for 1,3-propanediamine versus 1,4-butanediamine reveals an extraordinary > 60000-fold enhancement in affinity, which is the largest increment/CH2 ever observed in supramolecular chemistry. The present results in combination with our ESI-MS data reported recently unambiguously demonstrate that CB[6] exists in aqueous solution of alkali metal salts exclusively as a dicationic species, e. g. [CB[ 6]center dot 2Na](2+).
- Keywords
- complex stability; cucurbit[6]uril; calorimetry; alkanol; alkylamine; alkanediamine; HOST-GUEST COMPLEXES; ORGANIC-MOLECULES; AQUEOUS-SOLUTION; ALKALINE-EARTH; CUCURBITURIL; FAMILY; ION; CYCLODEXTRINS; CATIONS
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/23411
- DOI
- 10.1080/10610270600915292
- ISSN
- 1061-0278
- Article Type
- Article
- Citation
- SUPRAMOLECULAR CHEMISTRY, vol. 19, no. 39815, page. 39 - 46, 2007-01
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