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https://doi.org/10.5562/cca3885

Mechanism of Solvolyses of Substituted Benzyl Bromides in 80 % Ethanol

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


Puni tekst: engleski pdf 4.678 Kb

str. P1-P5

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Sažetak

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.

Ključne riječi

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

Hrčak ID:

276164

URI

https://hrcak.srce.hr/276164

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