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An investigation of the mechanism of single and double hydrogen atom transfer reactions in alkyl benzoates by the ortho effect
Author(s) -
Tajima Susumu,
Azami Tadashige,
Shizuka Haruo,
Tsuchiya Toshikazu
Publication year - 1979
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210140908
Subject(s) - chemistry , isopropyl , benzoates , benzoic acid , hydrogen atom , medicinal chemistry , alkyl , ethyl benzoate , protonation , hydrogen , methyl benzoate , stereochemistry , ion , organic chemistry , catalysis
Single and double hydrogen atom transfers in reactions (1) and (2) in the mass spectra of ethyl benzoate, isopropyl benzoate, and isobutyl benzoate have been investigated with reference to the ortho effect: (1) [C 6 H 5 CO 2 R] + ⋅ → [C 6 H 5 CO 2 H] + ⋅ ( m/z 122) + (R‐H); (2) [C 6 H 5 CO 2 R] + ⋅ → [C 6 H 5 CO 2 H 2 ] + ( m/z 123) + · (R‐2H). It is demonstrated that the intermediate ion [C 6 H 5 CO 2 H 2 ] + has the protonated benzoic acid structure with the hydrogen atom on the carbonyl group.