TY - JOUR
T1 - Ortho Effect in Electron Ionization Mass Spectrometry of N-Acylanilines Bearing a Proximal Halo Substituent
AU - Jariwala, Freneil B.
AU - Figus, Margaret
AU - Attygalle, Athula B.
PY - 2008/8
Y1 - 2008/8
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=48349104022&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=48349104022&partnerID=8YFLogxK
U2 - 10.1016/j.jasms.2008.05.004
DO - 10.1016/j.jasms.2008.05.004
M3 - Article
AN - SCOPUS:48349104022
SN - 1044-0305
VL - 19
SP - 1114
EP - 1118
JO - Journal of the American Society for Mass Spectrometry
JF - Journal of the American Society for Mass Spectrometry
IS - 8
ER -