title: Study on [(4-substituted benzoylamino)phenylmethyl]phosphonic acid diisopropyl esters under electrospray ionization tandem mass spectrometric conditions.
abstract: Phosphonate esters were synthesized and investigated by positive ion electrospray ionization mass spectrometry (ESI-MS) in conjunction with tandem mass spectrometry (MS/MS). It was found that for the sodiated adduct there were two novel rearrangement reactions, in which the phosphoryl oxygen atom migrated to the carbonyl carbon and a cleavage occurred at the amide bond, or a benzylamine fragment was lost and the phosphorus was reduced. However, when the methyl group substituted for the isopropyl group, these migrations were inhibited. A possible mechanism was proposed, and high-resolution mass spectrometry was applied to identify the formula of these novel ions. These results showed that ESI-MS is a useful tool for the structural determination of phosphonate esters.
authors.affiliation: The Key Laboratory for Chemical Biology of Fujian Province, Department of Chemistry, Xiamen University, Xiamen 361005, P. R. China.
authors.forename: Hua
authors.initials: H
authors.lastname: Fang
authors.forename: Mei-juan
authors.initials: MJ
authors.lastname: Fang
authors.forename: Chang-jin
authors.initials: CJ
authors.lastname: Zhu
authors.forename: Lin-na
authors.initials: LN
authors.lastname: Liu
authors.forename: Yu-fen
authors.initials: YF
authors.lastname: Zhao
mesh_terms: D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D053719:Tandem Mass Spectrometry / Q000379:methods*
chemical_list: D063065:Organophosphonates