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

doi:10.1021/ja011679p

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

52 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 language	English
Pages (from-to)	4287-4297
Number of pages	11
Journal	Journal of the American Chemical Society
Volume	124
Issue number	16
DOIs	https://doi.org/10.1021/ja011679p
Publication status	Published - 2002 Apr 24

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja011679p

Cite this

@article{5b439a9bdd6f4fc6997bd368da715b15,

title = "Self-complementarity of oligo-2-aminopyridines: A new class of hydrogen-bonded ladders",

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.",

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

year = "2002",

month = apr,

day = "24",

doi = "10.1021/ja011679p",

language = "English",

volume = "124",

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journal = "Journal of the American Chemical Society",

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publisher = "American Chemical Society",

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T1 - Self-complementarity of oligo-2-aminopyridines

T2 - A new class of hydrogen-bonded ladders

AU - Leung, Man Kit

AU - Mandal, Ashis B.

AU - Wang, Chih Chieh

AU - Lee, Gene Hsiang

AU - Peng, Shie Ming

AU - Cheng, Hsing Ling

AU - Her, Guor Rong

AU - Chao, Ito

AU - Lu, Hsiu Feng

AU - Sun, Ying Chieh

AU - Shiao, Mei Ying

AU - Chou, Pi Tai

PY - 2002/4/24

Y1 - 2002/4/24

N2 - 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.

AB - 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.

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

Abstract

ASJC Scopus subject areas

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CCDC 149603: Experimental Crystal Structure Determination

CCDC 149602: Experimental Crystal Structure Determination

CCDC 149604: Experimental Crystal Structure Determination

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

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 149603: Experimental Crystal Structure Determination

CCDC 149602: Experimental Crystal Structure Determination

CCDC 149604: Experimental Crystal Structure Determination

Cite this