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Theoretical Studies on Proton Transfer Reactions of 8‐Hydroxyquinoline Monomers and Dimers
Author(s) -
Zhao JiYang,
Zhou ZiYan,
Su ZhongMin,
Xie YuZhong,
Sun GuangYan,
Wu Xue
Publication year - 2006
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200690138
Subject(s) - chemistry , intramolecular force , dimer , tautomer , monomer , proton , isomerization , density functional theory , computational chemistry , reaction mechanism , hydrogen bond , 8 hydroxyquinoline , photochemistry , molecule , stereochemistry , organic chemistry , polymer , catalysis , physics , quantum mechanics
Density functional theory (DFT) of quantum chemistry method was employed to investigate proton transfer reactions of 8‐hydroxyquinoline (8‐HQ) monomers and dimers. By studying the potential energy curves of the isomerization, the most possible reaction pathway was found. The total energy of 8‐hydroxyquinoline was lower than that of quinolin‐8(1 H )‐one, whereas the order was reversed in dimers. The findings explained the contrary experimental phenomena. The minimum reaction barrier of intramolecular proton transfer was 47.3 kJ/mol while that in dimer was only 25.7 kJ/mol. Hence it is obvious that proton transfer reactions of 8‐HQ monomer have a considerable rate but it is easier to proceed for 8‐HQ dimer than monomers. It implied that the hydrogen bond played an important role in depressing the activation energy of reaction. The mechanism of the tautomerization was discussed on the basis of theoretical results.