The periodic table and the intrinsic barrier in SN2 reactions

Ren Yi, Harold Basch, Shmaryahu Hoz

Research output: Contribution to journalArticlepeer-review

44 Scopus citations

Abstract

The identity SN2 reactions on nitrogen (see eq 3) with nucleophiles having the general structure HnX- where X belongs to the group of nonmetallic elements which do not border the line separating them from the metallic elements (X = F, Cl, Br, I, O, S, Se, N, P, and C) were studied at the G2+ level. The results show that, similarly to the previously observed phenomenon for SN2 reaction on carbon (J. Am. Chem. Soc. 1999, 121, 7724), the Periodic Table, through the valence of the element X, controls the intrinsic barrier for the reaction. The average intrinsic barriers obtained for nitrogen substrates were 20, 27, 39, and 57 kcal/mol for the mono-, di-, tri-, and tetravalent X's, respectively. It is also concluded that the intrinsic barriers are similar for N- and C-based substrates and dimethyl substitution on both raises the intrinsic barrier by ca. 10 kcal/mol.

Original languageEnglish
Pages (from-to)5891-5895
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number17
DOIs
StatePublished - 23 Aug 2002

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