Macrocycles with two exclusive hydrogen-bonding modes

Min Kyung Chae, Geun Young Cha, Kyu Sung Jeong

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A series of large, 44-membered macrocycles 7a-e were synthesized and characterized, which display two different diagonal binding modes. The unsubstituted macrocycle 7a strongly binds naphthalene-2,6-dicarboxylate through hydrogen bonds with the association constant (Ka ± 15%) of 4500 M-1 in 40% (v/v) CD3CN/CDCl3 at 23 ± 1 °C. Introduction of an electron-withdrawing substituent (Cl) at all four corners increases the binding affinity (22,000 M-1 for 7b), while that of an electron-donating substituent (pyrrolidinyl) greatly decreases it (150 M-1 for 7c). The same propensity has been observed with macrocycles 7d and 7e bearing different substituents at two diagonal corners, suggesting that the relative population of the binding modes would be modulated by controlling the electron density of the aromatic ring.

Original languageEnglish
Pages (from-to)8217-8220
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number47
DOIs
Publication statusPublished - 2006 Nov 20

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Hydrogen Bonding
Hydrogen bonds
Bearings (structural)
Electrons
Carrier concentration
Association reactions
Hydrogen
Population
naphthalene

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Chae, Min Kyung ; Cha, Geun Young ; Jeong, Kyu Sung. / Macrocycles with two exclusive hydrogen-bonding modes. In: Tetrahedron Letters. 2006 ; Vol. 47, No. 47. pp. 8217-8220.
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Macrocycles with two exclusive hydrogen-bonding modes. / Chae, Min Kyung; Cha, Geun Young; Jeong, Kyu Sung.

In: Tetrahedron Letters, Vol. 47, No. 47, 20.11.2006, p. 8217-8220.

Research output: Contribution to journalArticle

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N2 - A series of large, 44-membered macrocycles 7a-e were synthesized and characterized, which display two different diagonal binding modes. The unsubstituted macrocycle 7a strongly binds naphthalene-2,6-dicarboxylate through hydrogen bonds with the association constant (Ka ± 15%) of 4500 M-1 in 40% (v/v) CD3CN/CDCl3 at 23 ± 1 °C. Introduction of an electron-withdrawing substituent (Cl) at all four corners increases the binding affinity (22,000 M-1 for 7b), while that of an electron-donating substituent (pyrrolidinyl) greatly decreases it (150 M-1 for 7c). The same propensity has been observed with macrocycles 7d and 7e bearing different substituents at two diagonal corners, suggesting that the relative population of the binding modes would be modulated by controlling the electron density of the aromatic ring.

AB - A series of large, 44-membered macrocycles 7a-e were synthesized and characterized, which display two different diagonal binding modes. The unsubstituted macrocycle 7a strongly binds naphthalene-2,6-dicarboxylate through hydrogen bonds with the association constant (Ka ± 15%) of 4500 M-1 in 40% (v/v) CD3CN/CDCl3 at 23 ± 1 °C. Introduction of an electron-withdrawing substituent (Cl) at all four corners increases the binding affinity (22,000 M-1 for 7b), while that of an electron-donating substituent (pyrrolidinyl) greatly decreases it (150 M-1 for 7c). The same propensity has been observed with macrocycles 7d and 7e bearing different substituents at two diagonal corners, suggesting that the relative population of the binding modes would be modulated by controlling the electron density of the aromatic ring.

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