Short communication, Note

https://doi.org/10.5562/cca3885

Mechanism of Solvolyses of Substituted Benzyl Bromides in 80 % Ethanol

Mirela Matić orcid.org/0000-0002-7812-2900 ; University of Zagreb, Faculty of Pharmacy and Biochemistry, Ante Kovačića 1, 10000 Zagreb, Croatia
Bernard Denegri orcid.org/0000-0001-6335-6723 ; University of Zagreb, Faculty of Pharmacy and Biochemistry, Ante Kovačića 1, 10000 Zagreb, Croatia
Tina Župan ; University of Zagreb, Faculty of Pharmacy and Biochemistry, Ante Kovačića 1, 10000 Zagreb, Croatia

Abstract

The mechanism of solvolysis of activated and deactivated benzyl bromides in 80 % ethanol at 25 °C has been investigated by using the Yukawa-Tsuno treatment and by correlating measured kinetic data with relative stabilities of corresponding benzyl carbocations calculated at the IEFPCM-M06-2X/6-311+G(3df,3pd) level of theory. Both correlation methods demonstrate that only benzyl bromides substituted with strong para-π-donors solvolyze by the SN1 mechanism whereas other activated and deactivated substrates solvolyze by the SN2 mechanism.

Keywords

benzyl bromide; IEFPCM; M06-2X; SN1; SN2; solvolysis; Yukawa-Tsuno

Hrčak ID:

276164

URI

https://hrcak.srce.hr/276164

Publication date:

26.4.2022.

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