Ortho Effect in Electron Ionization Mass Spectrometry of N-Acylanilines Bearing a Proximal Halo Substituent

Freneil B. Jariwala, Margaret Figus, Athula B. Attygalle

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

Electron ionization (EI) mass spectra are not very helpful for characterizing ortho, meta, and para isomers of underivatized haloanilines since their spectra are virtually identical. In contrast, when the amino group of chloro-, bromo-, or iodoanilines is transformed to an N-formyl, N-acetyl, or N-benzoyl derivative, the spectra of the derivatives reveal a highly dramatic loss of a halogen radical, instead of an HX elimination usually expected from an "ortho effect." For example, the spectra of N-formyl, N-acetyl, and N-benzoyl derivatives of ortho isomers of chloro-, bromo-, and iodoanilines show a very prominent peak at m/z 120, 134, and 196, respectively, for the loss of the corresponding halogen atom.

Original languageEnglish
Pages (from-to)1114-1118
Number of pages5
JournalJournal of the American Society for Mass Spectrometry
Volume19
Issue number8
DOIs
StatePublished - Aug 2008

Fingerprint

Dive into the research topics of 'Ortho Effect in Electron Ionization Mass Spectrometry of N-Acylanilines Bearing a Proximal Halo Substituent'. Together they form a unique fingerprint.

Cite this