Influence of Lewis acids on the symmetric SN2 reaction

Iñigo Iribarren, Cristina Trujillo Del Valle, Goar Sanchez Sanz, Eric Hénon, José Elguero, Ibon Alkorta

Research output: Contribution to journalArticlepeer-review

Abstract

This paper presents a theoretical analysis the effect of non-covalent interactions (NCI) in three different SN2 reactions (X–:CH3X → XCH3:X–, X = Cl, Br and I) has been theoretically analysed in the pre-reactive complexes, TS and products. A total of eighteen Lewis acids (LAs: FH, ClH, FCl, I2, SeHF, SeF2, PH2F, PF3, SiH3F, SiF4, BH3, BF3, BeH2, BeF2, LiH, LiF, Au2 and AgCl) interact with the halogen atom of the CH3X molecule. To analyse the strength of the non-covalent interactions, both the independent gradient model tool and electron density maps have been employed. The results reveal that in all cases, the interaction between the anion and the Lewis acid leads to an increase in the transition barriers compared to the parental reaction.
Original languageEnglish
Article number81
JournalTheoretical Chemistry Accounts
Volume142
Issue number8
DOIs
Publication statusPublished - 5 Aug 2023

Keywords

  • Electron density shifts
  • Independent gradient model
  • Lewis acid
  • Non-covalent interactions
  • S 2

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