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Synthesis, kinetic study, and reaction mechanism: Nucleophilic substitution reactions of butyl methyl chlorophosphate with substituted anilines and deuterated substituted anilines in acetonitrile

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This study demonstrated the kinetics of nucleophilic substitution reactions of butyl methyl chlorophosphate (2) with X-anilines (XC6H4NH2) and deuterated X-anilines (XC6H4ND2) in MeCN at 55.0 ± 0.1°C together with the general optimized method for the synthesis of 2 under mild conditions. Different spectroscopic characterizations revealed the formation of 2 with high purity. The free energy relationship with the substituents X in the anilines exhibited biphasic concavity upwards with a break point at X = H, which induced large negative ρX and small positive βX values. |

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