Issue 16, 2003

Nucleophilic identity substitution reactions. The reaction between ammonia and protonated amines

Abstract

The gas phase reactions between NH3 and the protonated amines MeNH3+, EtNH3+, PriNH3+, and ButNH3+ have been studied by high level ab initio methods. Mass spectrometric experiments yielded no significant reaction products; this result being consistent with the calculated reaction barriers. The potential energy profiles for both nucleophilic substitution (SN2) and elimination (E2) pathways have been investigated. Both back side Walden inversion (SNB) and front side (SNF) nucleophilic reaction profiles have been generated. The SNB reaction barriers are found to be higher for the more alkyl substituted reaction centres. Reaction barrier trends have been analysed and compared with the results of a similar study of the H2O–ROH2+ system (R = Me, Et, Pri, and But).

Graphical abstract: Nucleophilic identity substitution reactions. The reaction between ammonia and protonated amines

Supplementary files

Article information

Article type
Paper
Submitted
28 Feb 2003
Accepted
30 Jun 2003
First published
15 Jul 2003

Org. Biomol. Chem., 2003,1, 2943-2950

Nucleophilic identity substitution reactions. The reaction between ammonia and protonated amines

J. K. Laerdahl, L. Bache-Andreassen and E. Uggerud, Org. Biomol. Chem., 2003, 1, 2943 DOI: 10.1039/B302270F

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