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• W2570312704 abstract "This paper describes a simple optimized method for the synthesis of O-butyl phenyl phosphonochloridothioate (4) under mild conditions. The target compounds were characterized by 1H-nuclear magnetic resonance (NMR), 13C-NMR, and 31P-NMR spectroscopy, as well as mass spectroscopy. The apparent structure of 4 was confirmed by optimization using the B3LYP/6-311 + G(d,p) level in the Gaussian 09 program in acetonitrile. The nucleophilic substitution reactions of 4 with X-anilines (XC6H4NH2) and deuterated X-anilines (XC6H4ND2) were investigated kinetically in acetonitrile at 55.0°C. The free energy relationship with X in the anilines looked biphasic concave upwards with a break region between X = H and X = 3-MeO, giving large negative ρX and small positive βX values. The deuterium kinetic isotope effects were secondary inverse (kH/kD < 1: 0.789-0.995) and the magnitudes, (kH/kD), increased when the nucleophiles were changed from weakly basic to strongly basic anilines. A concerted SN2 mechanism is proposed on the basis of the selectivity parameters and the variation trend of the deuterium kinetic isotope effects with X." @default.
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• W2570312704 date "2017-01-05" @default.
• W2570312704 modified "2023-09-24" @default.
• W2570312704 title "Anilinolysis of O -butyl phenyl phosphonochloridothioate in acetonitrile: Synthesis, characterization, kinetic study, and reaction mechanism" @default.
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• W2570312704 doi "https://doi.org/10.1002/poc.3679" @default.
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