Kinetics and mechanism of the anilinolysis of dimethyl and diethyl chloro(thiono)phosphates

Dey NK; Hoque MEU; Kim CK; Lee BS; Lee HW

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Kinetics and mechanism of the anilinolysis of dimethyl and diethyl chloro(thiono)phosphates

机译：二甲基和二乙基氯（硫代）磷酸酯苯胺化反应的动力学和机理

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The deuterium kinetic isotope effects (KIEs) involving deuterated aniline nucleophiles (XC6H4ND2) are reported for the reactions of dimethyl chlorophosphate (1), dimethyl chlorothionophosphate (2), diethyl chlorophosphate (3) and diethyl chlorothionophosphate (4) in acetonitrile at 55.0 degrees C. The obtained k(H)/k(D) values are 0.798-0.979, 0.945-1.06, 0.714-0.919 and 1.01-1.10 for 1, 2,3 and 4, respectively. A concerted mechanism with dominant backside nucleophilic attack is proposed for the reactions of 1 and 3. A concerted mechanism involving partial frontside attack through a hydrogen-bonded four-centre-type transition state (TS) is proposed for the reactions of 2 and 4.

机译：据报道，氘化苯胺亲核试剂（XC6H4ND2）的氘动力学同位素效应（KIEs）在55.0摄氏度下在乙腈中进行了氯代二甲基氯代磷酸酯（1），二甲基氯代硫代磷酸二磷酸酯（2），氯代磷酸二乙酯（3）和氯代磷酸二乙酯（4）的反应。对于1、2、3和4，获得的k（H）/ k（D）值分别为0.798-0.979、0.945-1.06、0.714-0.919和1.01-1.10。针对1和3的反应，提出了具有主要的背面亲核进攻的协同机制。针对2和4的反应，提出了涉及通过氢键四中心型过渡态（TS）进行部分正面进攻的协同机制。

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《Journal of Physical Organic Chemistry》 |2008年第8期|共5页
作者
Dey NK; Hoque MEU; Kim CK; Lee BS; Lee HW;
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中图分类有机化学一般性问题;
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deuterium kinetic isotope effect; anilinolysis; dimethyl and diethyl chlorophosphates; dimethyl and diethyl chlorothionophosphates;

机译：氘动力学同位素效应;苯胺分解;氯代磷酸二甲酯和二乙酯;氯代硫代磷酸二甲酯和二乙酯;

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机译：二甲基和二乙基氯（硫代）磷酸酯苯胺化反应的动力学和机理
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Kinetics and mechanism of the anilinolysis of dimethyl and diethyl chloro(thiono)phosphates

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