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 language | English |
|---|---|
| Pages (from-to) | 8217-8220 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 47 |
| Issue number | 47 |
| DOIs | |
| Publication status | Published - 2006 Nov 20 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
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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 journal › Article
TY - JOUR
T1 - Macrocycles with two exclusive hydrogen-bonding modes
AU - Chae, Min Kyung
AU - Cha, Geun Young
AU - Jeong, Kyu Sung
PY - 2006/11/20
Y1 - 2006/11/20
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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U2 - 10.1016/j.tetlet.2006.09.127
DO - 10.1016/j.tetlet.2006.09.127
M3 - Article
AN - SCOPUS:33750004844
VL - 47
SP - 8217
EP - 8220
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 47
ER -