An Investigation of Structure of Intermediate Ions from Several Substituted Alkyl Benzoates by the ortho Effect and Kinetic Energy Release

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Single and double hydrogen atom transfers in reactions (1) and (2) are found in the mass spectra of n-propyl and n-butyl benzoates, and n-propyl and n-butyl p-hydroxy-benzoates. In contrast, only single hydrogen atom transfer is found in the mass spectra of n-propyl and n-bulyl salicylates and it is concluded that the hydrogen bond prevents the second hydrogen atom transfer. The kinetic energy release for the loss of water from the m/z 138 ion[C7H6O3]+ produced from ethyl and higher alkyl salicylates by a McLafferty rearrangement was nearly equal to that from the molecular ion of salicylic acid (m/z 138). The kinetic energy release for the loss of water from the m/z 137 ion[C7H7NO2]+ from ethyl o-aminobenzoate was also equal to that from the molecular ion of o-amino benzoic acid (m/z 137). However, the corresponding kinetic energy release from the m/z 136 ion[C8H8O2]+ from ethyl o-methylbenzoate was somewhat higher than that from the molecular ion of o-methyl benzoic acid (m/z 136).