A Computational Study on Water-assisted Ammonolysis of N-Methyl β-Sultam

高等学校化学研究 ›› 2006, Vol. 22 ›› Issue (1): 94-98.

A Computational Study on Water-assisted Ammonolysis of N-Methyl β-Sultam

HE Mao-xia, FENG Da-cheng, YU Ling-juan, CAI Zheng-ting

Institute of Theoretical Chemistry, Shandong University, Jinan 250100, P. R. China

收稿日期:2005-02-11 出版日期:2006-02-24 发布日期:2011-08-06
基金资助:
Supported by the National Natural Science Foundation of China(Nos. 20373034 and 20173032) and Ph.D. Special Research Foundation of the Ministry of Education of China.

A Computational Study on Water-assisted Ammonolysis of N-Methyl β-Sultam

HE Mao-xia, FENG Da-cheng, YU Ling-juan, CAI Zheng-ting

Institute of Theoretical Chemistry, Shandong University, Jinan 250100, P. R. China

Received:2005-02-11 Online:2006-02-24 Published:2011-08-06
Supported by:
Supported by the National Natural Science Foundation of China(Nos. 20373034 and 20173032) and Ph.D. Special Research Foundation of the Ministry of Education of China.

摘要/Abstract

摘要： The ring opening of β-sultam via an H₂O-assisted ammonolysis process was studied by using Density Functional Theory(DFT) method at the B3LYP/6-31G^* level as a further step in the theoretical investigation of the ammonolysis reaction of β-sultams. The calculated pathways are analogous to those previously described for the non-assisted ammonolysis reaction. Solvent effects were assessed by using the polarized continuum model(PCM) method. The results show that mode 1 and pathway a in channel Ⅱ are the most favorable ones in both the cases. The energy barrier of the cleavage of C-S bonds producing P1 is the highest among all the energy barriers. The presence of a solvent in the continuum model disfavors the reaction, whereas the participation of water in the ammonolysis reaction plays a positive role and reduces the active energy greatly. The relative energies of all the transition states in the assisted ammonolysis are 20-80 kJ/mol lower than those for the non-assisted reaction.

关键词: Ammonolysis, Water-assisted mechanism, Density Functional Theory(DFT), &beta, -Sultam

Abstract: The ring opening of β-sultam via an H₂O-assisted ammonolysis process was studied by using Density Functional Theory(DFT) method at the B3LYP/6-31G^* level as a further step in the theoretical investigation of the ammonolysis reaction of β-sultams. The calculated pathways are analogous to those previously described for the non-assisted ammonolysis reaction. Solvent effects were assessed by using the polarized continuum model(PCM) method. The results show that mode 1 and pathway a in channel Ⅱ are the most favorable ones in both the cases. The energy barrier of the cleavage of C-S bonds producing P1 is the highest among all the energy barriers. The presence of a solvent in the continuum model disfavors the reaction, whereas the participation of water in the ammonolysis reaction plays a positive role and reduces the active energy greatly. The relative energies of all the transition states in the assisted ammonolysis are 20-80 kJ/mol lower than those for the non-assisted reaction.

Key words: Ammonolysis, Water-assisted mechanism, Density Functional Theory(DFT), β-Sultam

HE Mao-xia, FENG Da-cheng, YU Ling-juan, CAI Zheng-ting. A Computational Study on Water-assisted Ammonolysis of N-Methyl β-Sultam[J]. 高等学校化学研究, 2006, 22(1): 94-98.

HE Mao-xia, FENG Da-cheng, YU Ling-juan, CAI Zheng-ting. A Computational Study on Water-assisted Ammonolysis of N-Methyl β-Sultam[J]. Chemical Research in Chinese Universities, 2006, 22(1): 94-98.

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A Computational Study on Water-assisted Ammonolysis of N-Methyl β-Sultam

A Computational Study on Water-assisted Ammonolysis of N-Methyl β-Sultam

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