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首页> 外文期刊>RSC Advances >Theoretical investigation of the chemoselectivity and synchronously pyrazole ring formation mechanism from ethoxymethylenemalononitrile and hydrazine hydrate in the gas and solvent phases: DFT, meta-GGA studies and NBO analysis
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Theoretical investigation of the chemoselectivity and synchronously pyrazole ring formation mechanism from ethoxymethylenemalononitrile and hydrazine hydrate in the gas and solvent phases: DFT, meta-GGA studies and NBO analysis

机译：气相和溶剂相中乙氧基亚甲基丙二腈和水合肼的化学选择性和吡唑环形成机理的理论研究：DFT，Meta-GGA研究和NBO分析

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In this work, structural and kinetic aspects of pyrazole (P) ring formation by the reaction of ethoxymethylenemalononitrile (R1) and hydrazine hydrate (R2) were theoretically studied in the gas and solvent phases. Two major possible mechanisms were considered. One of them was initiated by nucleophilic attack of nitrogen atom of R2 on carbon atom of C=C double bond of R1 (Route 1) and the other was started by nucleophilic attack of nitrogen atom of R2 on carbon atom of cyanide group in R1 (Route 2). In order to investigate the solvent effect on the reaction mechanism, all the possible paths were reconsidered in methanol as the solvent. Obtained results showed that the most probable path is route 2 in the gas and solvent phases. Theoretical studies showed that the chemoselectivity of the nucleophilic attack of nitrogen atom in the gas phase is similar to the solvent. Solvent was able to decrease the barrier energy of the rate determining step and enforce the reaction to proceed through subroute 5 of route 2.
机译：在这项工作中，理论上研究了在气相和溶剂相中乙氧基亚甲基丙二腈（R1）和水合肼（R2）反应形成吡唑（P）环的结构和动力学方面。考虑了两种主要的可能机制。其中一个是由R2的氮原子亲核攻击R1的C = C双键的碳原子引发的（路线1），另一个是由R2的氮原子亲核攻击R1的氰化物基团的碳原子引发的（路线2）。为了研究溶剂对反应机理的影响，在甲醇作为溶剂中重新考虑了所有可能的途径。所得结果表明，气相和溶剂相中最可能的路径是路径2。理论研究表明，气相中氮原子的亲核进攻的化学选择性与溶剂相似。溶剂能够降低速率确定步骤的势垒能，并使反应通过路线2的子路线5进行。

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