Self-complementarity of oligo-2-aminopyridines: A new class of hydrogen-bonded ladders

Man Kit Leung, Ashis B. Mandal, Chih Chieh Wang, Gene Hsiang Lee, Shie Ming Peng, Hsing Ling Cheng, Guor Rong Her, Ito Chao, Hsiu Feng Lu, Ying-Chieh Sun, Mei Ying Shiao, Pi Tai Chou

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

A new class of hydrogen-bonded ladders based on hydrogen-bonded dimerization of oligo-α-aminopryidines has been demonstrated. Jorgensen's model can be successfully applied to this hydrogen-bonding system in nonpolar solvents. The results show the competitive enthalpy/entropy compensation relationship upon dimerization. Although increasing the number of hydrogen-bonding interactions would enhance the hydrogen-bonding stabilization enthalpy, this stabilization enthalpy per unit would be partially sacrificed to compensate for the entropy loss due to dimerization. These results clearly support the importance of preorganization in designing hydrogen-bonding guest - host molecules.

Original languageEnglish
Pages (from-to)4287-4297
Number of pages11
JournalJournal of the American Chemical Society
Volume124
Issue number16
DOIs
Publication statusPublished - 2002 Apr 24

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Ladders
Hydrogen Bonding
Dimerization
Hydrogen
Hydrogen bonds
Enthalpy
Entropy
Stabilization
Molecules
alpha-aminopyridine

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Leung, M. K., Mandal, A. B., Wang, C. C., Lee, G. H., Peng, S. M., Cheng, H. L., ... Chou, P. T. (2002). Self-complementarity of oligo-2-aminopyridines: A new class of hydrogen-bonded ladders. Journal of the American Chemical Society, 124(16), 4287-4297. https://doi.org/10.1021/ja011679p

Self-complementarity of oligo-2-aminopyridines : A new class of hydrogen-bonded ladders. / Leung, Man Kit; Mandal, Ashis B.; Wang, Chih Chieh; Lee, Gene Hsiang; Peng, Shie Ming; Cheng, Hsing Ling; Her, Guor Rong; Chao, Ito; Lu, Hsiu Feng; Sun, Ying-Chieh; Shiao, Mei Ying; Chou, Pi Tai.

In: Journal of the American Chemical Society, Vol. 124, No. 16, 24.04.2002, p. 4287-4297.

Research output: Contribution to journalArticle

Leung, MK, Mandal, AB, Wang, CC, Lee, GH, Peng, SM, Cheng, HL, Her, GR, Chao, I, Lu, HF, Sun, Y-C, Shiao, MY & Chou, PT 2002, 'Self-complementarity of oligo-2-aminopyridines: A new class of hydrogen-bonded ladders', Journal of the American Chemical Society, vol. 124, no. 16, pp. 4287-4297. https://doi.org/10.1021/ja011679p
Leung, Man Kit ; Mandal, Ashis B. ; Wang, Chih Chieh ; Lee, Gene Hsiang ; Peng, Shie Ming ; Cheng, Hsing Ling ; Her, Guor Rong ; Chao, Ito ; Lu, Hsiu Feng ; Sun, Ying-Chieh ; Shiao, Mei Ying ; Chou, Pi Tai. / Self-complementarity of oligo-2-aminopyridines : A new class of hydrogen-bonded ladders. In: Journal of the American Chemical Society. 2002 ; Vol. 124, No. 16. pp. 4287-4297.
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