Identification of epoxide functionalities in protonated monofunctional analytes by using ion/molecule reactions and collision-activated dissociation in different ion trap tandem mass spectrometers

Journal of the American Society for Mass Spectrometry

Volumn 23, Issue 1, 2012, Pages 12-22

  Eismin, Ryan J ^a   Fu, Mingkun ^a   Yem, Sonoeun ^a   Widjaja, Fanny ^a   Kenttämaa, Hilkka I ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

Epoxides; Functional group selective; Ion molecule reactions; Phenyl epoxides; Trimethyl borate; vinyl epoxides

Indexed keywords

EPOXIDES; FUNCTIONAL-GROUP SELECTIVE; ION-MOLECULE REACTION; PHENYL EPOXIDES; TRIMETHYL; VINYL EPOXIDES;

AMIDES; CARBOXYLIC ACIDS; CYCLOTRONS; DISSOCIATION; ELECTRON CYCLOTRON RESONANCE; HYDROCARBONS; MASS SPECTROMETERS; MATHEMATICAL TRANSFORMATIONS; METHANOL; OXYGEN; PROPYLENE; PROTONATION; SPECTROMETRY;

IONS;

2,3 EPOXYBUTANE; ACETAMIDE; ACETONE; ALCOHOL; AMIDE; BORIC ACID; BUTYRIC ACID; CARBONYL DERIVATIVE; CARBOXYLIC ACID; DIETHYLAMINE; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; HEXANOIC ACID; HYDROCARBON; ISOPROPYLAMINE; METHANOL; N METHYLFORMAMIDE; N METHYLPROPIONAMIDE; N,N DIETHYLAMINE; N,N DIMETHYLACETAMIDE; N,N DIMETHYLFORMAMIDE; OXYGEN; PHENYL EPOXIDE; PROPIONAMIDE DERIVATIVE; PROPIONIC ACID; PROPYLAMINE; PROPYLENE OXIDE; TETRAHYDROFURAN; TRIMETHYL BORATE; UNCLASSIFIED DRUG; VINYL EPOXIDE;

ADDITION REACTION; ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; COLLISIONALLY ACTIVATED DISSOCIATION; CONTROLLED STUDY; ELIMINATION REACTION; ION CYCLOTRON RESONANCE MASS SPECTROMETRY; ION MOLECULE REACTION; ION TRAP MASS SPECTROMETRY; MASS SPECTROMETER; PROTON TRANSPORT; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

BORATES; EPOXY COMPOUNDS; ETHYL ETHERS; FOURIER ANALYSIS; IONS; METHANOL; OXYGEN; PROTONS; TANDEM MASS SPECTROMETRY;

EID: 84856204221     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-011-0249-y     Document Type: Article

References (37)

1. Luik, H., Johannes, I., Palu, V., Luik, L., Kruusement, K.: Transformation of Biomass Internal Oxygen at Varied Pyrolysis Conditions. J. Anal. Appl. Pyrol. 79, 121-127 (2007) (Pubitemid 46589630)
2. Kwon, K.C., Mayfield, H., Marolla, T., Nichols, B., Mashburn, M.: Catalytic Deoxygenation of Liquid Biomass for Hydrocarbon Fuels. Renew. Energ. 36, 907-915 (2011)
3. Peiris, D.M., Lam, W., Michael, S., Ramanathan, R.: Distinguishing N-oxide and Hydroxyl Compounds: Impact of Heated Capillary/heated Ion Transfer Tube in Inducing Atmospheric Pressure Ionization Source Decompositions. J. Mass Spectrom. 39, 600-606 (2004) (Pubitemid 38878316)
4. Winger, B.E., Kemp, C.A.J.: Characterization of Pharmaceutical Compounds and Related Substances by Using HPLC FTICR-MS and Tandem Mass Spectrometry. Am. Pharm. Rev. 4, 55-63 (2001)
5. de Hoffmann, E.: Tandem Mass Spectrometry: a Primer. J. Mass Spectrom. 31, 129-137 (1996) (Pubitemid 26064767)
6. McLafferty, F.W.: Tandem Mass Spectrometry (MS/MS): A Promising New Analytical Technique for Specific Component Determination in Complex Mixtures. Am. Chem. Soc. 13, 33-39 (1980)
7. Schroeder, M.J., Shabanowitz, J., Schwartz, J.C., Hunt, D.F., Coon, J.J.: A Neutral Loss Activation Method for Improved Phosphopeptide Sequence Analysis by Quadrupole Ion Trap Mass Spectrometry. Anal. Chem. 76(13), 3590-3598 (2004) (Pubitemid 38868819)
8. Levsen, K., Schwarz, H.: Gas-Phase Chemistry of Collisionally Activated Ions. Mass Spectrom. Rev. 2, 77-148 (1983)
9. Kenttämaa, H.I., Pachuta, R.R., Rothwell, A., Cooks, R.G.: Experimental-Study of the Potential-Energy Surface of the Protonated Cyclohexene Oxide Cyclohexanone System-Isomerization, Dissociation, and Ion Molecule Reactions of the Isolated Ions in the Gas-Phase. J. Am. Chem. Soc. 111, 1654-1665 (1989)
10. Brodbelt, J.S.: Analytical Applications of Ion-Molecule Reactions. Mass Spectrom. Rev. 16, 91-110 (1997) (Pubitemid 127552742)
11. Eichmann, E.S., Brodbelt, J.S.: Application of Site-Selective Ion-Molecule Reactions to the Analysis of the Cinchona Alkaloids. Org. Mass Spectrom. 28, 1608-1615 (1993)
12. Alvarez, E.J., Brodbelt, J.S.: Selective Ion-Molecule Reactions of Ether Reagent Ions with Nucleoside Antibiotics in a Quadrupole Ion Trap. J. Mass Spectrom. 30, 625-631 (1995)
13. Ramos, L.E., Cardoso, A.M., Correia, A.J.F., Nibbering, N.M.M.: Behavior of Arylalkylamines Toward Trimethyl Borate as a Gas-Phase Reagent. Int. J. Mass Spectrom. 203, 101-110 (2000) (Pubitemid 32063007)
14. Moraes, L.A.B., Gozzo, F.C., Eberlin, M.N., Vainiotalo, P.J.: Transacetalization with Acylium Ions. A Structurally Diagnostic Ion/Molecule Reaction for Cyclic Acetals and Ketals in the Gas Phase. J. Org. Chem. 62, 5096-5103 (1997) (Pubitemid 27328166)
15. Eberlin, M.N.: Structurally Diagnostic Ion/Molecule Reactions: Class and Functional-Group Identification by Mass Spectrometry. J. Mass Spectrom. 41, 141-156 (2006) (Pubitemid 43260154)
16. Meurer, E.C., Chen, H., Riter, L.S., Cooks, R.G.: Meerwein Reaction of Phosphonium Ions with Epoxides and Thioepoxides in the Gas Phase. J. Am. Soc. Mass Spectrom. 15, 398-405 (2004) (Pubitemid 38283884)
17. Ranatunga, T.D., Kenttämaa, H.I.: Gas-Phase Reactions of Dicoordicated Boron Cations with Alcohols. Inorg. Chem. 34, 18-27 (1995)
18. Ranatunga, T.D., Kennedy, J.M., Kenttämaa, H.I.: Disubstituted Boron Cleave Carbonyl Bonds. J. Am. Chem. Soc. 119, 5200-5207 (1997) (Pubitemid 27290714)
19. Kempen, E.C., Brodbelt, J.: Use of Trimethyl Borates as a Chemical Ionization Reagent for Analysis of Biologically Active Molecules. J. Mass Spectrom. 32, 846-854 (1997) (Pubitemid 27331424)
20. Watkins, M.A., Price, J.M., Winger, B.E., Kenttämaa, H.I.: Ion-Molecule Reactions for Mass Spectrometric Identification of Functional Groups in Protonated Oxygen-Containing Monofunctional Compounds. Anal. Chem. 76, 964-976 (2004) (Pubitemid 38235545)
21. Watkins, M.A., Winger, B.E., Shea, R.C., Kenttämaa, H.I.: Ion-Molecule Reactions for the Characterization of Polyols and Polyol Mixtures by ESI/FT-ICR Mass Spectrometry. Anal. Chem. 77, 1385-1392 (2005) (Pubitemid 40327878)
22. Somuramasami, J., Duan, P., Watkins, M.A., Winger, B.E., Kenttämaa, H.I.: Ion-Molecule Reactions of Trimethylborate Allow the Mass Spectrometric Identification and Counting of Functional Groups in Protonated Bifunctional Oxygen-Containing Compounds and Polyols. Int. J. Mass Spectrom. 265, 359-371 (2007)
23. Campbell, K.M., Watkins, M.A., Li, S., Fiddler, M.N., Winger, B., Kenttämaa, H.I.: Functional Group Selective Ion/Molecule Reactions: Mass Spectrometric Identification of the Amido Functionality in Protonated Monofunctional Compounds. J. Org. Chem. 72, 3159-3165 (2007) (Pubitemid 46668112)
24. Gronert, S., O'Hair, R.A.J.: Gas Phase Reactions of Trimethyl Borate with Phosphates and Their Noncovalent Complexes. J. Am. Soc. Mass Spectrom. 13, 1088-1098 (2002) (Pubitemid 36871603)
25. Ranatunga, T.D., Kenttämaa, H.I.: Dicoordinated Boron Cations Dehydrate Organic Ethers in the Gas-Phase. J. Am. Chem. Soc. 114, 8600-8604 (1992)
26. Suming, H., Yaozu, C., Longfei, J., Shuman, X.: Stereochemical Effects in Mass Spectrometry. Org. Mass Spectrom. 20, 719 (1985)
27. Habicht, S.C., Vinueza, N.R., Archibold, E.F., Duan, P., Kenttämaa, H.I.: Identification of the Carboxylic Acid Functionality by Using Electrospray Ionization and Ion-Molecule Reactions in a Modified Linear Quadruple Ion Trap Mass Spectrometer. Anal. Chem. 80, 3416-3421 (2008) (Pubitemid 351620729)
28. Dunbar, R.C.: Infrared Radiative Cooling of Gas-Phase Ions. Mass Spectrom. Rev. 11, 309-339 (1992)
29. Chen, L., Wang, T.C.L., Ricca, T.L., Marshall, A.G.: Phase-Modulated Stored Wave-Form Inverse Fourier-Transform Excitation for Trapped Ion Mass-Spectrometry. Anal. Chem. 59, 449-454 (1987)
30. Marshall, A.G., Wang, T.C.L., Ricca, T.L.: Tailored Excitation for Fourier Transform Ion Cyclotron Mass Spectrometry. J. Am. Chem. Soc. 107, 7893-7897 (1985)
31. Gauthier, J.W., Trautman, T.R., Jackson, D.B.: Sustained Off-Resonance Irradiation for Collision-Activated Dissociation Involving Fourier Transform Mass Spectrometry. Collision-Activated Dissociation Technique that Emulates Infrared Multiphoton Dissociation. Anal. Chim. Acta 246, 211-225 (1991)
32. Gronert, S.: Estimation of Effective Ion Temperature in a Quadrupole Ion Trap. J. Am. Soc. Mass Spectrom. 9, 845-848 (1998) (Pubitemid 34467736)
33. Gronert, S.: Quadrupole Ion Trap Studies of Fundamental Organic Reactions. Mass Spectrom. Rev. 24, 100-120 (2005) (Pubitemid 40146423)
34. Schwartz, J.C., Senko, M.W., Syka, J.E.P.: A Two-Dimensional Quadrupole Ion Trap Mass Spectrometer. J. Am. Soc. Mass Spectrom. 13, 659-669 (2002) (Pubitemid 36876020)
35. Satterfield, M., Brodbelt, J.S.: Site of Reaction of Pilocarpine. J. Am. Mass. Spectrom. 10, 209-216 (1999) (Pubitemid 34461247)
36. Hunter, E.P., Lias, S.G.: Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update. J. Phys. Chem. Ref. Data 27, 413-656 (1998)
37. Habicht, S.C., Vinueza, N.R., Amundson, L.M., Kenttämaa, H.I.: Comparison of Functional Group Selective Ion-molecule Reactions of Trimethyl Borate in Different Ion Trap Mass Spectrometers. J. Am. Soc. Mass Spectrom. 22, 520-530 (2011)