Self-complementarity of oligo-2-aminopyridines: a new class of hydrogen-bonded ladders.
A new class of hydrogen-bonded ladders based on hydrogen-bonded dimerization of oligo-alpha-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.
Leung
Man-kit
MK
Department of Chemistry, National Taiwan University, Taipei 106, Taiwan. mkleung@ms.ntu.edu.tw
Mandal
Ashis B
AB
Wang
Chih-Chieh
CC
Lee
Gene-Hsiang
GH
Peng
Shie-Ming
SM
Cheng
Hsing-Ling
HL
Her
Guor-Rong
GR
Chao
Ito
I
Lu
Hsiu-Feng
HF
Sun
Ying-Chieh
YC
Shiao
Mei-Ying
MY
Chou
Pi-Tai
PT