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*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

51 Citations (Scopus)


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
Issue number16
Publication statusPublished - 2002 Apr 24

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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