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  • 1
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    International Journal of Chemical Kinetics 30 (1998), S. 419-423 
    ISSN: 0538-8066
    Keywords: Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The aminolysis reactions of O-ethyl S-(Z-phenyl) dithiocarbonates (Z=p-CH3, H, p-Cl, and p-NO2) with anilines (AN) and N,N-dimethylanilines (DMA) in acetonitrile at 30.0°C are investigated. Relatively small values of βX (βnuc,0.4 ca. 0.7) and βZ (βlg -0.1 ca. -0.4) for both ANs and DMAs, significantly large kH/kD values (1.1 ca. 1.9) involving deuterated anilines, and large negative ρXZ values for ANs (-0.56) are interpreted to indicate a concerted mechanism for both ANs and DMAs but with a hydrogen bonded four-center type transition state (TS) for ANs. The relative leaving ability, k(Z=p-NO2)/k(Z=p-CH3), is smaller for ANs than for DMAs, especially for a weaker nucleophile (1.9 and 4.7 for AN and DMA, respectively, with X=p-Cl). This suggests that the rate enhancement by the hydrogen-bond formation in the four-center type TS for AN is greater for a weaker nucleofuge (Z=p-CH3), especially when the nucleophile (X=p-Cl) is weaker. © 1998 John Wiley & Sons, Inc. Int J Chem Kinet: 30: 419-423,1998
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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