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Pseudo ‐crown ether‐like structure by hydrogen‐bonded dimerization: A water complex with bis(2′‐hydroxyethyl) 2,6‐pyridinedicarboxylate in solid, solution, and gas phases
Author(s) -
Habata Yoichi,
Takeshita Makoto,
Fukuda Yoji,
Akabori Sadatoshi,
Bradshaw Jerald S.
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380613
Subject(s) - chemistry , dimer , molecule , chloroform , mass spectrum , titration , hydrogen bond , ligand (biochemistry) , water dimer , fourier transform infrared spectroscopy , mass spectrometry , hydrogen , electron ionization , crystallography , polymer chemistry , ionization , ion , organic chemistry , biochemistry , receptor , physics , chromatography , quantum mechanics
Abstract Dedicated to Professor Jerald S. Bradshaw Bis(2′‐hydroxyethyl) 2,6‐pyridinedicarboxylate (1) was prepared and the structure was characterized in solid (fourier transform‐ir and X‐ray analyses), in liquid ( 1 H and 13 C nmr titrations), and in the gas‐phase (fast atom bombardment (fab) and electron spray ionization (esi) ms). Two bis(2′‐hydroxyethyl) 2,6‐pyridinedicarboxylate molecules each with an included water molecule are bound together through hydrogen bonding to give a pseudo‐macrocycle in the solid state and in chloroform solution. The fab and esi mass spectra also suggested that ligand 1 forms a dimer in the gas‐phase.