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Citation: Wang Yan-Hua, Zou Jian-Wei, Hu Gui-Xiang, Zheng Ke-Wen, Yu Qing-Sen. Theoretical Studies on the Nucleophilic Additions of Mimic Compounds of Pyrroloquinoline Quinone with Ammonia[J]. Acta Physico-Chimica Sinica, ;2004, 20(09): 1129-1133. doi: 10.3866/PKU.WHXB20040914 shu

Theoretical Studies on the Nucleophilic Additions of Mimic Compounds of Pyrroloquinoline Quinone with Ammonia

1.
Department of Chemistry, Zhejiang University, Hangzhou　310027; Key Laboratory for Molecular Design and Nutrition Engineering of Ningbo City, Ningbo Institute of Technology, Zhejiang University, Ningbo　315104; College of Biology and Environment Protection, Zhejiang Shuren University, Hangzhou　310015

Received Date: 27 February 2004
Available Online: 15 September 2004

Nucleophilic additions of a series of mimic compounds of pyrroloquinoline quinone(PQQ) and their analogues with ammonia were investigated at the B3LYP/D95(d, p) level of theory in order to study the relationship between structure and reactivity. It is demonstrated that: (1) for the monocarbonyl system, the electrophilicity of the carbonyl carbon affects significantly the reactive energy barrier; (2) for the biscarbonyl system, the hydrogen bond, formed at the transition state between the hydrogen of the nuclephilic reagent ammonia and the ortho-carbonyl oxygen is crucial for reaction activation energy; (3) while the fused ring has little effect on the reactive barrier, the reaction activation energy can be significantly reduced by the hydrogen bond between H of ammonia and N1 atom in the fused hetercycle. Quantitatively, a od linear correlation has been found between the reaction activation energy and the angle (φ(OCN) ) between the attacked carbonyly and the N atom of the nucleophilic NH3 at the transition state.
- Cofactor PQQ;Density functional theory;Nucleophilic addition;　Hydrogen bond
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