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Computational study of epoxy‐amine reactions
Author(s) -
Okumoto Satoshi,
Yamabe Shinichi
Publication year - 2002
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.10138
Subject(s) - chemistry , methylamine , amine gas treating , tetramer , amine oxide , pentamer , nucleophile , dimer , oxide , trimer , molecule , ethylene oxide , hydrogen bond , photochemistry , polymer chemistry , organic chemistry , catalysis , biochemistry , alkyl , polymer , copolymer , enzyme
Density functional theory calculations were carried out for the title reactions. Ethylene oxide and methylamine were adopted as reactants. Amine clusters (dimer, trimer, tetramer, and pentamer) were considered, because the combination of one oxide and one amine molecule gave a large activation energy. An amine tetramer was found to react favorably with the oxide via various zwitterionic intermediates. A back‐side S N 2 nucleophilic attack of one amine and the subsequent proton relay up to the front side provide a stabilized reaction field. The amine‐alcohol mixed reactant may react readily with the oxide, because the alcoholic OH group is in contact with the oxide oxygen with the strong hydrogen‐bond stabilization. © 2002 Wiley Periodicals, Inc. J Comput Chem 24: 244–253, 2003