TY - JOUR
T1 - Influence of Lewis acids on the symmetric SN2 reaction
AU - Iribarren, Iñigo
AU - Trujillo Del Valle, Cristina
AU - Sanchez Sanz, Goar
AU - Hénon, Eric
AU - Elguero, José
AU - Alkorta, Ibon
PY - 2023/8/5
Y1 - 2023/8/5
N2 - 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.
AB - 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.
KW - Electron density shifts
KW - Independent gradient model
KW - Lewis acid
KW - Non-covalent interactions
KW - S 2
UR - http://www.scopus.com/inward/record.url?scp=85167407931&partnerID=8YFLogxK
U2 - 10.1007/s00214-023-03013-9
DO - 10.1007/s00214-023-03013-9
M3 - Article
SN - 1432-881X
VL - 142
JO - Theoretical Chemistry Accounts
JF - Theoretical Chemistry Accounts
IS - 8
M1 - 81
ER -