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Citation: Li Yong-Hong, Chen Li-Ping, Xu Wen-Yuan, Hong San-Guo. Reaction Mechanism of the Gas-phase Elimination of 2-bromopropionic Acid[J]. Acta Physico-Chimica Sinica, ;2003, 19(05): 389-392. doi: 10.3866/PKU.WHXB20030502 shu

Reaction Mechanism of the Gas-phase Elimination of 2-bromopropionic Acid

1.
Department of Chemistry, Jiangxi Normal University, Nanchang　330027

Received Date: 4 July 2002
Available Online: 15 May 2003

The gas-phase elimination of 2-bromopropionic acid was investigated using density functional theory (DFT) method. Molecular structures were calculated at the B3LYP/6-31G** level. The results obtained show that the gas-phase elimination of 2-bromopropionic acid proceeds via a semi-polar five-membered cyclic transition state, where the acidic H of the group COOH assisted the leaving Br atom, and the carboxylic oxygen stabilized this transition state. The single-point energies of all optimized molecular structures by B3LYP/6-31G** were counted at B3LYP/6-311＋＋G (3df,3pd) level. The activation energy(Ea1=ETS1－ERe)of the rate-controlling step obtained at B3LYP/6-311＋＋G (3df,3pd) level was 189.5 kJ•mol－1,which is closely correlated with the available experimental data(180.3±3.4) kJ•mol－1.The relative error is 5.08％.
- 2-bromopropionic acid;Gas-phase elimination;Density functional theory(DFT);Reaction mechanism
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