Gas-phase ion/molecule reactions between dimethoxyphosphonium ions and aromatic hydrocarbons

Rapid Communications in Mass Spectrometry : RCM
Eric LeclercJean-Pierre Morizur

Abstract

Ion/molecule reactions between O=P(OCH(3))(2)(+) phosphonium ions and six aromatic hydrocarbons (benzene, toluene, 1,2,4-trimethylbenzene, naphthalene, acenaphthylene and fluorene) were performed in a quadrupole ion trap mass spectrometer. The O=P(OCH(3))(2)(+) phosphonium ions, formed by electron impact from neutral trimethyl phosphite, were found to react with aromatic hydrocarbons (ArHs) to give (i) an adduct [ArH, O=P(OCH(3))(2)](+) and (ii) for ArHs which have an ionization energy below or equal to 8.14 eV, a radical cation ArH(+ *) by charge transfer reaction. Collision-induced dissociation experiments, which produce fragment ions other than the O=P(OCH(3))(2)(+) ions, indicate that the adduct ions are covalent species. Isotope-labeled ArHs were used to elucidate fragmentation mechanisms. The charge transfer reactions were investigated using density functional theory at the B3LYP/6-311 + G(3df,2p)//B3LYP/6-31G(d,p) level of theory. The potential energy surface obtained from B3LYP/6-31G(d,p) calculations for the reaction between O=P(OCH(3))(2)(+) and benzene is described.

References

May 1, 1999·Journal of the American Society for Mass Spectrometry·L E Ramírez-ArizmendiH I Kenttämaa

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Citations

Mar 5, 2004·Journal of the American Society for Mass Spectrometry·Eduardo C MeurerMarcos N Eberlin
Feb 16, 2005·Journal of Mass Spectrometry : JMS·Eric LeclercJean-Pierre Morizur
Jul 12, 2002·Journal of Mass Spectrometry : JMS
Sep 25, 2004·Mass Spectrometry Reviews·Scott Gronert
Aug 27, 2003·European Journal of Mass Spectrometry·Pham-Cam NamMinh Tho Nguyen
Aug 8, 2021·Physical Chemistry Chemical Physics : PCCP·Mincheng YuShaodong Zhou

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