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231224s2012 xx |||||o 00| ||eng c |
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|a 10.1002/jcc.21967
|2 doi
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|a pubmed25n0709.xml
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|a (DE-627)NLM212648047
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|a (NLM)22042734
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|a DE-627
|b ger
|c DE-627
|e rakwb
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|a eng
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|a Gao, Jie Ying
|e verfasserin
|4 aut
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|a Mechanism for the reaction of 2-naphthol with N-methyl-N-phenyl-hydrazine suggested by the density functional theory investigations
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|c 2012
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|a Text
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|2 rdacontent
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|a ƒaComputermedien
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|2 rdamedia
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|a ƒa Online-Ressource
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|2 rdacarrier
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|a Date Completed 12.07.2012
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|a Date Revised 15.11.2012
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|a published: Print-Electronic
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|a Citation Status MEDLINE
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|a Copyright © 2011 Wiley Periodicals, Inc.
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|a For the first time the computed mechanisms for the novel reaction of 2-naphthol with N-methyl-N-phenylhydrazine, leading to 1-amino-2-naphthol (Tang et al., J Am Chem Soc 2008, 130, 5840), have been investigated using the density functional theory. Four distinct possible pathways were evaluated: two amination mechanisms with the attack of NH(2) group respectively at the α-position C1 and β-position C3 atoms of 2-naphthol (pathways 1 and 2) as well as two rearrangement processes with displacement of the phenolic hydroxyl group followed by the benzidine-like rearrangement at the α-position C1 and β-position C3 atoms of 2-naphthol, respectively (pathways 3 and 4). Solvent effect has been tested based on the optimized geometries of the stationary points in solution at the B3LYP/PCM/6-31+G(d,p) level of theory with an averaged dielectric constant of binary solvent. Single-point energies of the optimized structures have been calculated using three hybrid density functionals, B3LYP, MPW3LYP, and B3PW91 with the 6-311++G(3df,2p) basis set. Our computed results clearly manifest that pathway 1 (α-amination) has the highest possibility to occur, with the Gibbs free energies being lower by 6 to 20 kcal/mol compared with the other three pathways, which leads to 1-amino-2-naphthol and N-methylaniline as products. It is in excellent agreement with the experimental observation
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|a Journal Article
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|a Research Support, Non-U.S. Gov't
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|a Amines
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|a N-methyl-N-phenyl-hydrazine
|2 NLM
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|a Naphthols
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|a Phenylhydrazines
|2 NLM
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|a 2-naphthol
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|a P2Z71CIK5H
|2 NLM
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|a Zhang, Cheng Hua
|e verfasserin
|4 aut
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|a Luo, Mei Ming
|e verfasserin
|4 aut
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|a Kim, Chan Kyung
|e verfasserin
|4 aut
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|a Chu, Wei
|e verfasserin
|4 aut
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|a Xue, Ying
|e verfasserin
|4 aut
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|i Enthalten in
|t Journal of computational chemistry
|d 1984
|g 33(2012), 2 vom: 15. Jan., Seite 220-30
|w (DE-627)NLM098138448
|x 1096-987X
|7 nnns
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|g volume:33
|g year:2012
|g number:2
|g day:15
|g month:01
|g pages:220-30
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|u http://dx.doi.org/10.1002/jcc.21967
|3 Volltext
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