Mechanism of solvolysis of substituted benzyl chlorides in aqueous ethanol (CROSBI ID 300918)
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Denegri, Bernard ; Matić, Mirela ; Vaško, Monika
engleski
Mechanism of solvolysis of substituted benzyl chlorides in aqueous ethanol
The mechanism of solvolyses of activated ortho-, meta- and para-substituted benzyl chlorides in aqueous ethanol has been studied by using the Hammett-Brown and Yukawa-Tsuno treatments as well as by correlating logarithms of solvolysis rate constants with relative stabilities of corresponding benzyl carbocations in water calculated at the IEFPCM-M06–2X/6-311+G(3df, 3pd) level of theory. Benzyl chlorides containing strong conjugative electron-donors in the para- position solvolyze by the SN1 mechanism, whereas other activated benzyl chlorides solvolyze by the SN2 mechanism via loose transition states.
benzyl chloride ; solvolysis ; SN1 mechanism ; SN2 mechanism ; Hammett-Brown correlation ; DFT
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