Ring Versus Nitrogen Protonation of Anilines

Author(s): Robert Flammang, Noemie Dechamps, Laurent Pascal, Yves Van Haverbeke, Pascal Gerbaux, Pham-Cam Nam, Minh Tho Nguyen.

Journal Name: Letters in Organic Chemistry

Volume 1 , Issue 1 , 2004

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Ionization of mixtures of halogenobenzenes and ammonia under chemical ionization conditions affords isomeric (N or C4) protonated anilines. The N-protonated species are dominantly produced by ionmolecule reactions of mass-selected ionized halogenobenzenes with ammonia or in electrospray conditions. Quantum chemical calculations confirm that the N-protonation in aniline is marginally favored, by about 4 kJ mol-1, over the C4-protonation.

Keywords: aniline proton affinity, chemical ionization, electrospray ionization, ion-molecule reactions, collision-induced dissociations

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Article Details

Year: 2004
Page: [23 - 30]
Pages: 8
DOI: 10.2174/1570178043488725

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