Selective adduct formation by furan chemical ionization reagent in gas chromatography ion trap mass spectrometry.

The analytical potential of furan as a chemical ionization (CI) reagent was evaluated for selectivity with nine monosubstituted naphthalene compounds. The ion-molecule reactions of furan and tetrahydrofuran (THF) were compared with those of methane, methanol and acetonitrile (prominently producing [M + H](+) ion base peaks) with naphthalene compounds in chemical ionization mass spectrometry (CI-MS). Reactions with furan predominantly show M(+) and [M + 39](+) ions. Based on this phenomenon, investigations were carried out for some of the molecular factors such as proton affinity, substituent effects and the preferred site of [C(3)H(3)](+) ion attachment that influence reactivity in furan CI. High selectivity with different substituents is observed in the formation of [M + 39](+) adduct ion, suggesting its usefulness as selective ionization reagent liquid. The selectivity and sensitivity are illustrated in the analysis of mixture of amino acids. Furthermore, the structure determination and reaction mechanism study is characterized by collision-activated dissociation experiments in CI-MS/MS and CI-MS/MS/MS.

[1]  I. Jamall,et al.  Organ-specific effects of naphthalene on tissue peroxidation, glutathione peroxidases and superoxide dismutase in the rat , 2004, Archives of Toxicology.

[2]  Y. Ling,et al.  Chemical ionization of substituted naphthalenes using tetrahydrofuran as a reagent in gas chromatography with ion trap mass spectrometry. , 2003, Rapid communications in mass spectrometry : RCM.

[3]  John M. Challinor,et al.  Review: the development and applications of thermally assisted hydrolysis and methylation reactions , 2001 .

[4]  B. Munson.  Development of chemical ionization mass spectrometry , 2000 .

[5]  W. Ding,et al.  Analysis of nonylphenol polyethoxylates and their degradation products in river water and sewage effluent by gas chromatography-ion trap (tandem) mass spectrometry with electron impact and chemical ionization. , 1998, Journal of chromatography. A.

[6]  S. Prabhakar,et al.  Acetone chemical ionization mass spectrometry , 1998 .

[7]  P. Fleurat‐Lessard,et al.  Mass Spectrometric Differentiation of Isomeric Polycyclic Aromatic Hydrocarbons by Chemical Ionization with Diethylether, Tetrahydrofuran and Dimethylcarbonate , 1997 .

[8]  R. Harvey,et al.  Polycyclic Aromatic Hydrocarbons , 1997 .

[9]  J. Brodbelt.  Analytical applications of ion-molecule reactions , 1997 .

[10]  C. Minero,et al.  Sub-parts-per-billion determination of nitro-substituted polynuclear aromatic hydrocarbons in airborne particulate matter and soil by electron capture-Tandem mass spectrometry , 1996, Journal of the American Society for Mass Spectrometry.

[11]  R. Tjeerdema,et al.  Comparative disposition and biotransformation of naphthalene in fresh- and seawater-acclimated striped bass (Morone saxatilis). , 1995, Xenobiotica; the fate of foreign compounds in biological systems.

[12]  M. Vairamani.  Acetone chemical ionization studies. VII‐acetylation of some aromatic compounds , 1993 .

[13]  J. Brodbelt,et al.  Examination of Ortho effects in the collisionally activated dissociation of closed‐shell aromatic ions , 1992 .

[14]  M. Harkey,et al.  Simultaneous quantitation of cocaine and its major metabolites in human hair by gas chromatography/chemical ionization mass spectrometry. , 1991, Journal of analytical toxicology.

[15]  C. Liou,et al.  SELECTIVE ADDUCT FORMATION BY DIMETHYL ETHER CHEMICAL IONIZATION IN A QUADRUPOLE ION TRAP MASS SPECTROMETER AND A CONVENTIONAL ION SOURCE , 1991 .

[16]  B. Munson,et al.  Quantitation using benzene in gas chromatography/chemical ionization mass spectrometry , 1991 .

[17]  D. Garland,et al.  Effects of naphthalene metabolites on cultured cells from eye lens. , 1991, Free radical biology & medicine.

[18]  M. Vairamani,et al.  Acetone chemical ionization studies: Olefins† , 1990 .

[19]  M. Vairamani,et al.  Unusual positive ion reagents in chemical ionization mass spectrometry , 1990 .

[20]  R. Cooks,et al.  Charge stripping and the site of cationization of substituted aromatic compounds , 1986 .

[21]  Joel F. Liebman,et al.  Evaluated Gas Phase Basicities and Proton Affinities of Molecules; Heats of Formation of Protonated Molecules , 1984 .

[22]  R. Cooks,et al.  Site of gas-phase cation attachment. Protonation, methylation, and ethylation of aniline, phenol, and thiophenol , 1983 .

[23]  O. Prakash,et al.  Mass spectral studies. Part 13. Novel use of crown ethers in chemical ionization mass spectrometry , 1983 .

[24]  T. Keough.  Dimethyl ether as a reagent gas for organic functional group determination by chemical ionization mass spectrometry , 1982 .

[25]  D. Brown,et al.  Evidence for cytochrome P-450 mediated metabolism in the bronchiolar damage by naphthalene. , 1982, Chemico-biological interactions.

[26]  A. Ferrer-Correia,et al.  The use of ion‐molecule reactions in the mass spectrometric location of double bonds , 1976 .

[27]  F. H. Field,et al.  Chemical Ionization Mass Spectrometry. I. General Introduction , 1966 .

[28]  H. J. Dick,et al.  Transplacental naphthalene poisoning. , 1959, American journal of obstetrics and gynecology.

[29]  E. Corner,et al.  Biochemical studies of toxic agents. VII. The metabolism of naphthalene in animals of different species. , 1954, The Biochemical journal.