Open AccessProton−Lithium Binding Behavior of Tris(2-((pyrid-2-ylmethyl)uredio)ethyl)amine
Author(s) -
Chih-Feng Liao,
Jun-Liang Lai,
Jau-An Chen,
Hung-Ting Chen,
Hsing-Ling Cheng,
GuorRong Her,
Jen Kuan Su,
Yu Wang,
Gene Hsiang Lee,
Mankit Leung,
ChihChieh Wang
Publication year - 2001
Publication title -
the journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/jo001221q
Subject(s) - chemistry , nitromethane , protonation , amine gas treating , tris , electrospray ionization , lithium (medication) , perchlorate , medicinal chemistry , lithium perchlorate , mass spectrometry , salt (chemistry) , inorganic chemistry , ion , organic chemistry , electrochemistry , chromatography , medicine , biochemistry , electrode , endocrinology
Tris(2-((pyrid-2-ylmethyl)uredio)ethyl)amine (2) and its perchlorate salt, 2.HClO(4), bind with Li+ in nitromethane in a 1:1 fashion. The stability constants of K(Li+) and K(H)(Li+) were found to be 112 +/- 25 and 130 +/- 30 M(-)(1) in CD(3)NO(2), respectively. Formation of the 1:1 complexes were further evidenced by electrospray ionization mass spectrometry (ESI-MS). The slight increase, or at least the same order of magnitude, of K(H)(Li+) compared to K(Li+) points to a remarkable preorganization of the protonated podand in 2.HClO(4), that essentially overcomes the increased Columbic repulsion occurring on complexation to Li+.
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