Self-Complementarity of Oligo-2-aminopyridines: A New Class of Hydrogen-Bonded Ladders | Zendy

Mankit Leung | Zendy; Ashis Baran Mandal | Zendy; ChihChieh Wang | Zendy; GeneHsiang Lee | Zendy; ShieMing Peng | Zendy; Hsing-Ling Cheng | Zendy; GuorRong Her | Zendy; Ito Chao | Zendy; HsiuFeng Lu | Zendy; YingChieh Sun | Zendy; Mei-Ying Shiao | Zendy; PiTai Chou | Zendy

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Self-Complementarity of Oligo-2-aminopyridines: A New Class of Hydrogen-Bonded Ladders

Author(s) -

Mankit Leung,

Ashis Baran Mandal,

ChihChieh Wang,

GeneHsiang Lee,

ShieMing Peng,

Hsing-Ling Cheng,

GuorRong Her,

Ito Chao,

HsiuFeng Lu,

YingChieh Sun,

Mei-Ying Shiao,

PiTai Chou

Publication year - 2002

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja011679p

Subject(s) - chemistry , hydrogen bond , enthalpy , complementarity (molecular biology) , hydrogen , molecule , entropy (arrow of time) , thermodynamics , crystallography , organic chemistry , physics , genetics , biology

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.

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