A molecular receptor that selectively binds dihydrogen phosphate

Tae Hoon Kwon, Kyu-Sung Jeong

Research output: Contribution to journalArticle

58 Citations (Scopus)

Abstract

A dihydrogen phosphate-binding receptor (4) containing both hydrogen bond donors and acceptors has been prepared by incorporating two pyridyl units to a preorganized biindole scaffold. Receptor 4 strongly and selectively binds dihydrogen phosphate via multiple hydrogen bonds with an association constant (Ka) of 1.1 × 105 M-1 in CH3CN at 22 ± 1 °C. The high selectivity toward the target anion over other anions is proven to be due to two additional hydrogen bonds between the phosphate hydroxyl groups and the pyridyl nitrogens, each of which increases the complex stability by the free energy of 1.6 kcal/mol. This result clearly demonstrates that a selective receptor for a polyprotic anion can be developed by combining both hydrogen bond donors and acceptors.

Original languageEnglish
Pages (from-to)8539-8541
Number of pages3
JournalTetrahedron Letters
Volume47
Issue number48
DOIs
Publication statusPublished - 2006 Nov 27

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Hydrogen
Hydrogen bonds
Phosphates
Anions
Scaffolds
Hydroxyl Radical
Free energy
Nitrogen
Association reactions

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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A molecular receptor that selectively binds dihydrogen phosphate. / Kwon, Tae Hoon; Jeong, Kyu-Sung.

In: Tetrahedron Letters, Vol. 47, No. 48, 27.11.2006, p. 8539-8541.

Research output: Contribution to journalArticle

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AB - A dihydrogen phosphate-binding receptor (4) containing both hydrogen bond donors and acceptors has been prepared by incorporating two pyridyl units to a preorganized biindole scaffold. Receptor 4 strongly and selectively binds dihydrogen phosphate via multiple hydrogen bonds with an association constant (Ka) of 1.1 × 105 M-1 in CH3CN at 22 ± 1 °C. The high selectivity toward the target anion over other anions is proven to be due to two additional hydrogen bonds between the phosphate hydroxyl groups and the pyridyl nitrogens, each of which increases the complex stability by the free energy of 1.6 kcal/mol. This result clearly demonstrates that a selective receptor for a polyprotic anion can be developed by combining both hydrogen bond donors and acceptors.

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