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Theoretical study of one‐carbon unit transfer between methyl‐AICA and N 1 ‐methyl‐ N 1 ‐acryloyl‐formamide
Author(s) -
Qiao QingAn,
Cai ZhengTing,
Feng DaCheng,
Jiang YuanSheng
Publication year - 2004
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.20201
Subject(s) - intermolecular force , chemistry , formamide , molecule , proton , hydrogen bond , transition state , computational chemistry , organic chemistry , physics , catalysis , quantum mechanics
The mechanism of one‐carbon unit transfer between 1‐methyl‐5‐amino‐4‐carboxamide imidazole (M‐AICA) and N 1 ‐methyl‐ N 1 ‐acryloyl‐formamide (the model molecule of 10‐f‐H4F) is investigated by the Hartree–Fock and DFT methods, respectively, at the 6‐31G* basis level. There are two different channels for the proton transfer, resulting in two reaction pathways with different properties. The results indicate that both channels can complete the reaction, but path a is slightly favored due to its lower active energy barrier. Furthermore, the influence of 4‐carboxamindde in M‐AICA is also discussed. This group can stabilize the reactant and intermediates, and reduce the active energy barrier through the intermolecular hydrogen bond. The intermolecular hydrogen bond results in an enlarged conjugation system and makes the transition states more stable. Our results are in agreement with experiments. © 2004 Wiley Periodicals, Inc. Int J Quantum Chem, 2005