Biindolyl-based molecular clefts that bind anions by hydrogen-bonding interactions

Kyu-Sung Jeong, Kyoung-Jin Chang, Min Kyung Chae, Changsoon Lee, Ji-Yeon Lee

Research output: Contribution to journalArticle

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Abstract

Molecular clefts were synthesized from 2,2′-biindolyl scaffold that contains good hydrogen bond donors of two indole NHs. The molecular clefts were systematically modified in two different manners to increase binding affinities toward chloride. The association constant dramatically increased when additional hydrogen-bonding sites of two benzamide units were incorporated to the biindolyl scaffold. For example, the association constants of 1a and 1b are 5.1 × 103 and 1.4 × 104 M−1 in CH3CN at 22 ± 1 °C, while reference molecule 10 having only two indole NHs showed the association constant of 340 M−1 under the same conditions. When the biindolyl backbone was structurally preorganized, the binding affinities toward anions were further increased with additional stabilization energy (−ΔΔG) of 2.0 ± 0.2 kcal/mol).
Original languageEnglish
Pages (from-to)6385-6388
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number36
DOIs
Publication statusPublished - 2006 Sep 4

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Hydrogen Bonding
Anions
Hydrogen bonds
Association reactions
Scaffolds
Chlorides
Hydrogen
Stabilization
Molecules
indole
benzamide

Cite this

Jeong, Kyu-Sung ; Chang, Kyoung-Jin ; Chae, Min Kyung ; Lee, Changsoon ; Lee, Ji-Yeon. / Biindolyl-based molecular clefts that bind anions by hydrogen-bonding interactions. In: Tetrahedron Letters. 2006 ; Vol. 47, No. 36. pp. 6385-6388.
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abstract = "Molecular clefts were synthesized from 2,2′-biindolyl scaffold that contains good hydrogen bond donors of two indole NHs. The molecular clefts were systematically modified in two different manners to increase binding affinities toward chloride. The association constant dramatically increased when additional hydrogen-bonding sites of two benzamide units were incorporated to the biindolyl scaffold. For example, the association constants of 1a and 1b are 5.1 × 103 and 1.4 × 104 M−1 in CH3CN at 22 ± 1 °C, while reference molecule 10 having only two indole NHs showed the association constant of 340 M−1 under the same conditions. When the biindolyl backbone was structurally preorganized, the binding affinities toward anions were further increased with additional stabilization energy (−ΔΔG) of 2.0 ± 0.2 kcal/mol).",
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Biindolyl-based molecular clefts that bind anions by hydrogen-bonding interactions. / Jeong, Kyu-Sung; Chang, Kyoung-Jin; Chae, Min Kyung; Lee, Changsoon; Lee, Ji-Yeon.

In: Tetrahedron Letters, Vol. 47, No. 36, 04.09.2006, p. 6385-6388.

Research output: Contribution to journalArticle

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T1 - Biindolyl-based molecular clefts that bind anions by hydrogen-bonding interactions

AU - Jeong, Kyu-Sung

AU - Chang, Kyoung-Jin

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AU - Lee, Ji-Yeon

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AB - Molecular clefts were synthesized from 2,2′-biindolyl scaffold that contains good hydrogen bond donors of two indole NHs. The molecular clefts were systematically modified in two different manners to increase binding affinities toward chloride. The association constant dramatically increased when additional hydrogen-bonding sites of two benzamide units were incorporated to the biindolyl scaffold. For example, the association constants of 1a and 1b are 5.1 × 103 and 1.4 × 104 M−1 in CH3CN at 22 ± 1 °C, while reference molecule 10 having only two indole NHs showed the association constant of 340 M−1 under the same conditions. When the biindolyl backbone was structurally preorganized, the binding affinities toward anions were further increased with additional stabilization energy (−ΔΔG) of 2.0 ± 0.2 kcal/mol).

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