1,721,179 research outputs found
Functional Group Selective Ion-molecule Reactions
No full textThe mechanistic details and potential applications of ion-molecule reactions were studied. Gas phase ion-molecule reactions was placed at the center of attention in mass spectrometry. The combination of conventional and new ionization and multiple-stage mass spectrometry techniques provide access for mass spectrometrists to a world of gaseous ions, reaction environments, and ion characterization methods. Functional group selective ion-molecule reactions will certainly found increasing applications in a variety of fields.1314Staley, R.H., Corderman, R.R., Foster, M.S., Beauchamp, J.L., (1974) J. Am. Chem. Soc., 96, p. 1260Moraes, L.A.B., Eberlin, M.N., (2000) Chem. Eur. J., 6, p. 897Kenttamaa, H.I., Cooks, R.G., (1989) J. Am. Chem. Soc., 111, p. 4122Moraes, L.A.B., Eberlin, M.N., (2002) J. Mass Spectrom., 37, p. 162Eberlin, M.N., Cooks, R.G., (1993) J. Am. Chem. Soc., 115, p. 9226Meurer, E.C., Eberlin, M.N., (2001) Int. J. Mass Spectrom., 210-211, p. 469Carvalho, M., Gozzo, F.C., Mendes, M.A., Sparrapan, R., Kascheres, C., Eberlin, M.N., (1998) Chem. Eur. J., 4, p. 1161Moraes, L.A.B., Eberlin, M.N., (1996) J. Org. Chem., 61, p. 8726Moraes, L.A.B., Gozzo, F.C., Eberlin, M.N., (1997) J. Org. Chem., 62, p. 5096H. Chen, X. Zheng, R. G. Cooks, unpublished resultsEberlin, M.N., Cooks, R.G., (1993) Org. Mass Spectrom., 28, p. 679Thompson, R.S., Guler, L.P., Nelson, E.D., Yu, Y.-Q., Kenttamaa, H.L., J. Org. Chem., , in pressStirk, K.M., Orlowski, J.C., Leeck, D.T., Kenttamaa, H.I., (1992) J. Am. Chem. Soc., 114, p. 8604Ramos, L.E., Cardoso, A.M., Ferrer Correia, A.J., Nibbering, N.M.M., (2000) Int. J. Mass Spectrom., 203, p. 101Kempen, E.C., Brodbelt, J., (1997) J. Mass Spectrom., 32, p. 846O'Hair, R.A.J., Reid, G.E., (2000) J. Am. Soc. Mass Spectrom., 111, p. 244Reid, G.E., Tichy, S.E., Pérez, J., O'Hair, R.A.J., Simpson, R.J., Kenttamaa, H.I., (2001) J. Am. Chem. Soc., 123, p. 1184Cooks, R.G., (2002) 50th Annual Conference on Mass Spectrometry and Allied Topics, , Monday Plenary Lecture, Orlando, Jun
Gas-phase Polar Cycloadditions
No full textThe dilute gas-phase environment of mass spectrometers provides versatile and convenient medium in which chemists can form a great variety of ionic species and study their intrinsic reactivity exploring reaction mechanisms and screening for new reactions and their applications. Recent and illustrative examples of gas-phase polar cycloadditions of even and odd-electrons ions, which have been observed (some for the first time) in the solvent- and counter ion-free environment of mass spectrometers, are presented. Synthetic and analytical applications of such reactions and correlations with analogous reactions observed in solution are also discussed. © 2004 Elsevier B.V. All rights reserved.2353263278Carruthers, W., Cycloadditon Reactions in Organic Synthesis, p. 1990. , PergamonDiels, O., Alder, K., (1928) Justus Liebigs Ann. Chem., 460, p. 98(1997) IUPAC Compendium of Chemical Terminology, Second Ed.Schmidt, R.R., (1973) Angew. Chem. Int. Edit., 12, p. 212Bauld, N.L., Bellville, D.J., Harirchian, B., Lorenz, K.T., Pabon Jr., R.A., Reynolds, D.W., Wirth, D.D., Marsh, B.K., (1987) Acc. Chem. Res., 20, p. 371Dass, C., (1990) Mass Spectrom. Rev., 9, p. 1Gronert, S., (2001) Chem. Rev., 101, p. 329Kuck, D., Mormann, M., (2002) The Chemistry of Dienes and Polyenes, 2. , Rappoport, Z.WileyHeinrich, N., Koch, W., Morrow, J.C., Schwarz, H., (1988) J. Am. Chem. Soc., 110, p. 6332Wilkins, C.L., Gross, M.L., (1971) J. Am. Chem. Soc., 93, p. 895Van Doorn, R., Nibbering, N.M.M., Ferrer-Correia, A.J.V., Jennings, K.R., (1978) Org. Mass Spectrom., 13, p. 729Vairamani, M., Mirza, U., Srinivas, R., (1990) Mass Spectrom. Rev., 9, p. 253Einhorn, J., Duffault, J.M., Virelizier, H., Tabet, J.C., (1988) Rapid Commun. Mass Spectrom., 2, p. 112Colorado, A., Barket, D.J., Hurst, J.M., Shepson, P.B., (1998) Anal. Chem., 70, p. 5129Bouchoux, G., Salpin, J.-Y., (1994) Rapid Commun. Mass Spectrom., 8, p. 325Bouchoux, G., Nguyen, M.T., Salpin, J.-Y., (2000) J. Phys. Chem., 104, p. 5778Grützmacher, H.-F., Barkow, A., (1997) Acta Chem. Scand., 51, p. 619Becker, H., Javahery, G., Petrie, S., Bohme, D.K., (1994) J. Phys. Chem., 98, p. 5591Shay, B.J., Eberlin, M.N., Cooks, R.G., Wesdemiotis, C., (1992) J. Am. Soc. Mass Spectrom., 3, p. 518Goerbbert, D.J., Liu, X., Wenthold, P.G., (2004) J. Am Soc. Mass Spectrom., 15, p. 114Hammerum, S., (1988) Mass Spectrom. Rev., 7, p. 123Stirk, K.M., Kiminkinen, M.L.K., Kenttämaa, H.I., (1992) Chem. Rev., 92, p. 1649Yates, B.F., Bouma, W.J., Radom, L., (1986) Tetrahedron, 42, p. 6225Moraes, L.A.B., Eberlin, M.N., (1998) J. Am. Chem. Soc., 120, p. 11136Eberlin, M.N., Sorrilha, A.E.P.M., Gozzo, F.C., Pimpim, R., (1997) J. Am. Chem. Soc., 119, p. 3550Lange, C., (1993) Org. Mass Spectrom., 28, p. 1285Mourgues, P., Audier, H.E., Hammerum, S., (1994) Rapid Commun. Mass Spectrom., 8, p. 53Gerbaux, P., Haverbeke, Y.V., Flammang, R., (2003) J. Am. Soc. Mass Spectrom., 14, p. 241Olah, G.A., Reddy, V.P., Prakash, G.K.S., (1992) Chem. Rev., 92, p. 69Holman, R.W., Plocica, J., Blair, L., Giblin, D., Gross, M.L., (2001) J. Phys. Org. Chem., 14, p. 17Eberlin, M.N., (1997) Mass Spectrom. Rev., 16, p. 113Eberlin, M.N., Mass Spectrom. Rev., , submitted for publicationEberlin, M.N., Cooks, R.G., (1993) J. Am. Chem. Soc., 115, p. 9226Meurer, E.C., Eberlin, M.N., (2002) J. Mass Spectrom., 37, p. 146Meurer, E.C., Moraes, L.A.B., Eberlin, M.N., (2001) Int. J. Mass Spectrom., 212, p. 445Eberlin, M.N., Majumdar, T.K., Cooks, R.G., (1992) J. Am. Chem. Soc., 114, p. 2884Juliano, V.J., Gozzo, F.C., Eberlin, M.N., Kascheres, C., (1996) Anal. Chem., 68, p. 1328Sharifi, M., Einhorn, J., (1999) Int. J. Mass Spectrom., 190-191, p. 253Eberlin, M.N., Morgon, N.H., Yang, S.S., Shay, B.J., Cooks, R.G., (1995) J. Am. Soc. Mass Spectrom., 6, p. 1Eberlin, M.N., Basher, M., Riveros, J.M., J. Mass Spectrom, , submitted for publicationGozzo, F.C., Sorrilha, A.E.P.M., Eberlin, M.N., (1996) J. Chem. Soc. Perkin Trans., p. 587Lu, L., Yang, S.S., Wang, Z., Cooks, R.G., Eberlin, M.N., (1995) J. Mass Spectrom., 30, p. 581Lemos, A.D., Sparrapan, R., Eberlin, M.N., (2003) J. Mass Spectrom., 38, p. 305Brodbelt, J.S., (1997) Mass Spectrom. Rev., 16, p. 91Keough, T., (1982) Anal. Chem., 54, p. 2540Ma, L., Liu, Z., Wang, W., Guo, X., Liu, S., (1999) J. Phys. Chem. a, 103, p. 8634Van Tilborg, M.W.E.M., Van Doorn, R., Nibbering, N.M.M., (1980) Org. Mass Spectrom., 15, p. 152Gozzo, F.C., Eberlin, M.N., (1999) J. Org. Chem., 64, p. 2188Kauffmann, T., (1965) Angew. Chem., 77, p. 557Sparrapan, R., Mendes, M.A., Carvalho, M., Eberlin, M.N., (2000) Chem. Eur. J., 6, p. 321Eberlin, M.N., Augusti, R., J. Mass Spectrom., , submitted for publicationD'Oca, M.G.M., Moraes, L.A.B., Pilli, R.A., Eberlin, M.N., (2001) J. Org. Chem., 66, p. 3854Needleman, S.B., Chang-Kuo, M.C., (1962) Chem. Rev., 62, p. 45Tomazela, D.M., Moraes, L.A.B., D'Oca, M.G.M., Pilli, R.A., Eberlin, M.N., (2002) J. Org. Chem., 67, p. 4652Van Pelt, C.K., Brenna, J.T., (1999) Anal. Chem., 71, p. 1981Pelt, C.K., Carpenter, B.K., Brenna, J.T., (1999) J. Am. Soc. Mass. Spectrom., 10, p. 1253Bernardi, F., Cacace, F., Petris, G., Pepi, F., Rossi, I., Troiani, A., (2000) Chem. Eur. J., 6, p. 537Boger, D.L., Weinreb, S.N., (1987) Hetero Diels-Alder Methodology in Organic Synthesis, , H.H. Wasserman (Ed.), New York, Academic PressAugusti, R., Gozzo, F.C., Moraes, L.A.B., Sparrapan, R., Eberlin, M.N., (1998) J. Org. Chem., 63, p. 4889Meurer, E.C., Moraes, L.A.B., Eberlin, M.N., (2001) Int. J. Mass Spectrom., 212, p. 445Meurer, E.C., Sparrapan, R., Eberlin, M.N., (2003) J. Mass Spectrom., 38, p. 1075Meurer, E.C., Chen, H., Riter, L., Cotte-Rodriguez, I., Eberlin, M.N., Cooks, R.G., (2004) Chem. Commun., p. 40Cowley, A.H., (1985) R.A. Kemp. Chem. Rev., 85, p. 367Solovieva, S.E., Gruner, M., Antipin, I.S., Habicher, W.D., Konovalov, A.I., (2001) Org. Lett., 3, p. 1299Gevrey, S., Taphanel, M.-H., Morizur, J.-P., (1998) J. Mass Spectrom., 33, p. 399Sabino, A.A., Eberlin, M.N., Moraes, L.A.B., Laali, K.K., (2003) Org. Biomol. Chem., 1, p. 395Moraes, L.A.B., Eberlin, M.N., Laali, K.K., (2001) Organometallics, 20, p. 4863Bakhtiar, R., Drader, J.D., Jacobson, D.B., (1992) J. Am. Chem. Soc., 114, p. 8304Schroeter, K., Schalley, C.A., Wesendrup, R., Schöder, D., Schwarz, H., (1997) Organometallics, 16, p. 986Chen, Q., Sioma, C., Kan, S.Z., Freiser, B.S., (1998) Int. J. Mass Spectrom., 180, p. 231Fenn, J.B., Mann, M., Meng, C.K., Wong, S.F., Whitehouse, C.M., (1989) Science, 246, p. 64Huang, E.C., Wachs, T., Conboy, J.J., Henion, J.D., (1990) Anal. Chem., 62, p. 713Hilderling, C., Adlhart, C., Chen, P., (1998) Angew. Chem. Int. Ed., 37, p. 2685Chen, P., (2003) Angew. Chem. Int. Ed., 42, p. 2832Sabino, A.A., MacHado, A.H.L., Correia, C.R.D., Eberlin, M.N., (2004) Angew. Chem. Int. Ed., 43, p. 2514Meurer, E.C., Santos, L.S., Pilli, R.A., Eberlin, M.N., (2003) Org. Lett., 5, p. 1391Choi, S.H., Cooley, R.B., Hakemian, A.S., Larrabee, Y.C., Bunt, R.C., Maupas, S.D., Muller, J.G., Burrows, C.J., (2004) J. Am. Chem. Soc., 126, p. 591Schuster, D.I., Cao, J.R., Kaprinidis, N., Wu, Y.H., Jensen, A.W., Lu, Q.Y., Wang, H., Wilson, S.R., (1996) J. Am. Chem. Soc., 118, p. 5639Meyer, S., Metzger, J.O., (2003) Anal. Bioanal. Chem., 377, p. 1108Meyer, S., Koch, R., Metzger, J.O., (2003) Angew. Chem. Int. Ed., 42, p. 4700Meurer, E.C., Sabino, A.A., Eberlin, M.N., (2003) Anal. Chem., 75, p. 4701Wentrup, C., Heilmayer, W., Kollenz, G., (1994) Synthesis, 343, p. 1219Eberlin, M.N., Moraes, L.A.B., J. Mass Spectrom., , submitted for publicatio
Absolute And General Assignment Of Constitutional Isomers By Mass Spectrometry: The Case Of Methylpiperidines [atribuição Absoluta E Geral De Isômeros Constitucionais Por Espectrometria De Massas: O Caso Das Metilpiperidinas]
No full textAn absolute method is described via mass spectrometry (MS) for the structural assignment of isomers within the class of methylpiperidines. The method explores both the unimolecular and bimolecular gas phase behavior of structurally diagnostic fragment ions (SDFI). For the methylpiperidnes, the isomeric 2-methyl, 3-methyl and 4-methyl 2-azabutadienyl cations are found to function as SDFI. These fragment ions are expected to be formed from all members within the class, to be stable and to retain the structural information of the precursor molecule, and to not interconvert into one another. To characterize these SDFI, both the collision induced dissociation (CID) in argon and bimolecular ion/molecule chemistry with ethyl vinyl ether were compared.3511721Zahedi-Tabrizi, M., Fariba, T., Moosavi-Tekyeh, Z., Alireza, J., Tayyari, S.F., (2006) Spectrochim. Acta, 65 (PART A), p. 387Tao, W.A., Gozzo, F.C., Cooks, R.G., (2001) Anal. Chem., 73, p. 1692Ramesh, M., Raju, B., Srinivas, R., Sureshbabu, V.V., Narendra, N., Vasantha, B., (2010) J. Mass Spectrom., 45, p. 1461Harvey, D.J., Jaeken, J., Butler, M., Armitage, A.J., Rudd, P.M., Dwek, R., (2010) J. Mass Spectrom., 45, p. 528Rainone, R., Malaspina, T., Xavier, L.A., Riveros, J.M., (2010) Eur J. Mass Spectrom., 16, p. 379Correra, T.C., Riveros, J.M., (2010) J. Phys. Chem. A, 114, p. 11910Fileti, E.E., Moraes, P.R.P., Domingues, L., Riveros, J.M., (2007) J. Mass Spectrom., 42, p. 1310Crotti, A.E.M., Lopes, J.L.C., Lopes, N.P., (2005) J. Mass Spectrom., 40, p. 1030Furtado, N.A.J.C., Vessecchi, R., Tomaz, J.C., Galembeck, S.E., Bastos, J.K., Lopes, N.P., Crotti, A.E.M., (2007) J. Mass Spectrom., 42, p. 1279Crotti, A.E.M., Bronze-Uhle, E.S., Nascimento, P.G.B.D., Donate, P.M., Galembeck, S.E., Vessecchi, R., Lopes, N.P., (2009) J. Mass Spectrom., 44, p. 1733Carvalho, M., Gozzo, F.C., Mendes, M.A., Sparrapan, R., Kascheres, C., Eberlin, M.N., (1998) Chem.-Eur. J., 4, p. 1161Gozzo, F.C., Eberlin, M.N., (1999) J. Org. Chem., 64, p. 2188Moraes, L.A.B., Sabino, A.A., Meurer, E.C., Eberlin, M.N., (2005) J. Am. Soc. Mass Spectrom., 16, p. 431Da Rocha, L.L., Sparrapan, R., Augusti, R., Eberlin, M.N., (2004) J. Mass Spectrom., 39, p. 1176Begala, M., Tocco, G., Meli, G., Podda, G., Urru, S.A.M., (2009) J. Mass Spectrom., 44, p. 245Benassi, M., Eberlin, M.N., (2010) J. Am. Soc. Mass Spectrom., 21, p. 2041Benassi, M., Corilo, Y.E., Uria, D., Augusti, R., Eberlin, M.N., (2009) J. Am. Soc. Mass Spectrom., 20, p. 269Benassi, M., Eberlin, M.N., Anais EletrôNicos do Segundo Congresso da Sociedade Brasileira de Espectrometria de Massas, p. 200. , Campinas, BrasilAugusti, R., Gozzo, F.C., Moraes, L.A.B., Sparrapan, R., Eberlin, M.N., (1998) J. Org. Chem., 63, p. 4889Meurer, E.C., Eberlin, M.N., (2001) Int. J. Mass Spectrom., 210, p. 469Schnermann, M.J., Romero, F.A., Hwang, I., Nakamaru-Ogiso, E., Yagi, T., Boger, D.L., (2006) J. Am. Chem. Soc., 128, p. 11799Tietze, L.F., Kettschau, G., (1997) Em Stereoselective Heterocyclic Synthesis, , Metz P. ed.Springer-verlag: Berlin, cap. 1Venturini, A., Joglar, J., Fustero, S., Gonzalez, J., (1997) J. Org. Chem., 62, p. 3919Zhao, F.L., Liu, J.T., (2005) J. Org. Chem., 70, p. 3801Barluenga, J., Tomas, M., Ballesteros, A., Lopez, L.A., (1991) J. Org. Chem., 56, p. 5680Meurer, E.C., Sparrapan, R., Eberlin, M.N., (2003) J. Mass Spectrom., 38, p. 1075Juliano, V.F., Gozzo, F.C., Eberlin, M.N., Kascheres, C., Do Lago, C.L., (1996) Anal. Chem., 68, p. 1328Eberlin, M.N., (1997) Mass Spectrom. Rev., 16, p. 113Budzikiewicz, H., Djerassi, C., Williams, D.H., (1967) Mass Spectrometry of Organic Compounds, , Holden-Day Inc: San FranciscoMclafferty, F.W., Turecek, F., (1993) Interpretation of Mass Spectra, , 4 th ed. University Science Books: SausalitoEberlin, M.N., (2006) J. Mass Spectrom., 41, p. 141Meurer, E.C., Sparrapan, R., Eberlin, M.N., (2003) J. Mass Spectrom., 38, p. 1075Kenttämaa, H.I., Pachuta, R.R., Rothwell, A.P., Cooks, R.G., (1989) J. Am. Chem. Soc., 111, p. 1654Kenttämaa, H.I., Cooks, R.G., (1989) J. Am. Chem. Soc., 111, p. 4122Meurer, E.C., Chen, H., Riter, L., Cotte-Rodriguez, I., Eberlin, M.N., Cooks, R.G., (2004) Chem. Commun., 1, p. 4
The Proton-bound Dimer Of Acetone [2]
No full text[No abstract available]401127128Derrick, P.J., (1982) Mass Spectrom. Rev., 2, p. 285Nourse, B.D., Cooks, R.G., (1991) Int. J. Mass Spectrom. Ion Processes, 106, p. 249Dang, T.T., Motell, E.L., Travers, M.J., Clifford, E.P., Ellison, G.B., DePuy, C.H., Bierbaum, V.M., (1993) Int. J. Mass Spectrom. Ion Processes, 123, p. 171O'Hair, R.A.J., Gronert, S., Williams, T.D., (1994) Org. Mass Spectrom., 29, p. 151Norman, K., McMahon, T.B., (1999) Int. J. Mass Spectrom., 182-183, p. 381Schröder, D., Semialjac, M., Schwarz, H., (2004) Int. J. Mass Spectrom., 223, p. 103Gozzo, F.C., Eberlin, M.N., (2001) J. Mass Spectrom., 36, p. 1140Eberlin, M.N., (1997) Mass Spectrom. Rev., 16, p. 113Juliano, V.F., Gozzo, F.C., Eberlin, M.N., Rascheres, C., Do Lago, C.L., (1996) Anal. Chem., 68, p. 1328Santos, L.S., Pavam, C.H., Almeida, W.P., Coelho, F., Eberlin, M.N., (2004) Angew. Chem. Int. Ed., 43, p. 4330Sabino, A.A., Machado, A.H.L., Correia, C.R.D., Eberlin, M.N., (2004) Angew. Chem. Int. Ed., 43, p. 2514Eberlin, M.N., Kotiaho, T., Shay, B.J., Yang, S.S., Cooks, R.G., (1994) J. Am. Chem. Soc., 116, p. 2457Yang, S.S., Wong, P., Ma, S.G., Cooks, R.G., (1996) J. Am. Soc. Mass Spectrom., 7, p. 198Meurer, E.C., Gozzo, F.C., Augusti, R., Eberlin, M.N., (2003) Eur. J. Mass Spectrom., 9, p. 295Denault, J.W., Wang, F., Cooks, R.G., Gozzo, F.C., Eberlin, M.N., (2000) J. Phys. Chem. A, 104, pp. 11 290Chen, G., Cooks, R.G., Corpuz, E., Scott, L.T., (1996) J. Am. Soc. Mass Spectrom., 7, p. 61
Structurally Diagnostic Ion-molecule Reactions: Acylium Ions With α-, β- And γ-hydroxy Ketones
No full textGas-phase reactions of four acylium ions and a thioacylium ion with three isomeric α-, β- and γ-hydroxy ketones are performed by pentaquadrupole mass spectrometric experiments. Novel structurally diagnostic reactions are observed, and found to correlate directly with interfunctional group separation. All five ions tested (CH3CO+, CH2=CHCO+, PhCO+, (CH3)2NCO+ and (CH3)2NCS+) react with the γ-hydroxy ketone (5-hydroxy-2-pentanone) to form nearly exclusively a cyclic oxonium ion of m/z 85 that formally arises from hydroxy anion abstraction. With the β-hydroxy ketone (4-hydroxy-2-pentanone), CH2=CHCO+, PhCO+ and (CH3)2NCO+ form adducts that undergo fast cyclization via intramolecular water displacement, yielding resonance-stabilized cyclic dioxinylium ions. With the α-hydroxy ketone (3-hydroxy-3-methyl-2-butanone), PhCO+, (CH3)2NCO+ and (CH3)2NCS+ form stable adducts. Evidence that these adducts display cyclic structures is provided by the triple-stage mass spectra of the (CH3)2NCS+ adduct; it dissociates to (CH3)2NCO+ via a characteristic reaction-dissociation pathway that promotes sulfur-by-oxygen replacement. If cyclizations are assumed to occur with intramolecular anchimeric assistance, relationships between structure and reactivity are easily recognized. Copyright © 2001 John Wiley & Sons, Ltd.372162168Kemp, W., (1970) Qualitative Organic Analysis, , McGraw-Hill: New YorkMcLafferty, F.W., (1983) Tandem Mass Spectrometry, , (ed). Wiley: New YorkBusch, K.L., Glish, G.L., McLuckey, S.A., (1988) Mass Spectrometry/Mass Spectrometry: Techniques and Applications of Tandem Mass Spectrometry, , VCH: New YorkFarrar, J.M., Saunders W.H., Jr., (1988) Techniques for the Study of Ion/Molecule Reactions, , (eds). Wiley: New YorkBrodbelt, J.S., (1997) Mass Spectrom. Rev., 16, p. 91Green, M.K., Lebrilla, C.B., (1997) Mass Spectrom. Rev., 16, p. 53Eberlin, M.N., (1997) Mass Spectrom. Rev., 16, p. 113Filippi, A., Giardini, A., Piccirillo, S., Speranza, M., (2000) Int. J. Mass Spectrom., 198, p. 137Gronert, S., (2001) Chem. Rev., 101, p. 329Olah, G.A., Gramain, A., White, A.M., (1976) Carbonium Ions, Olah GA, Schleyer PvR, , (eds). Wiley: New YorkAl-Talib, M., Tashtoush, H., (1990) Org. Prep. Proceed. Int., 22, p. 1Eberlin, M.N., Cooks, R.G., (1993) J. Am. Chem. Soc., 115, p. 9226Grandinetti, F., Pepi, F., Ricci, A., (1996) Chem. Eur. J., 2, p. 495Moraes, L.A.B., Gozzo, F.C., Eberlin, M.N., Vainiotalo, P., (1997) J. Org. Chem., 62, p. 5096Creaser, C.S., Williamson, B.L., (1998) Eur. Mass Spectrom., 4, p. 103Sharifi, M., Einhorn, J., (1999) Int. J. Mass Spectrom., 190-191, p. 253Grützmacher, H.F., Dohmeier-Fischer, S., (1998) Int. J. Mass Spectrom. Ion. Processes, 179-180, p. 207Reid, G.E., Tichy, S.E., Pérez, J., O'Hair, R.A.J., Simpson, R.J., kenttämaa, H.I., (2001) J. Am. Chem. Soc., 123, p. 1184Meurer, E.C., Eberlin, M.N., (2001) Int. J. Mass Spectrom., 210-211, p. 469Juliano, V.F., Kascheres, C., Gozzo, F.C., Eberlin, M.N., Lago, C.L., (1996) Anal. Chem., 68, p. 1328Eberlin, M.N., Majumdar, T.K., Cooks, R.G., (1992) J. Am. Chem. Soc., 114, p. 2884Moraes, L.A.B., Pimpim, R.S., Eberlin, M.N., (1996) J. Org. Chem., 61, p. 8726Tiernan, T.O., Futrell, J.H., (1968) J. Phys. Chem., 72, p. 3080Schwartz, J.C., Wade, A.P., Enke, C.G., Cooks, R.G., (1990) Anal. Chem., 62, p. 1809Kim, J.K., Findlay, M.C., Henderson, W.G., Caserio, M.C., (1973) J. Am. Chem. Soc., 95, p. 2184Wysocki, V.H., Burinsky, D.J., Cooks, R.G., (1985) J. Org. Chem., 50, p. 1287Eichmann, E.S., Brodbelt, J.S., (1993) Org. Mass Spectrom., 28, p. 665Freitas, M.A., O'Hair, R.A.J., Willians, T.D., (1997) J. Org. Chem., 62, p. 6112Heck, A.J.R., de Koning, L.J., Nibbering, N.M.M., (1993) Org. Mass Spectrom., 28, p. 245O'Hair, R.A.J., Freitas, M.A., Gronet, S., Schmidt, J.A.R., Williams, T.D., (1995) J. Org. Chem., 60, p. 1990Vais, V., Etinger, A., Mandelbaum, A., (1999) J. Mass Spectrom., 34, p. 755O'Hair, R.A., Gronet, S., (1999) Int. J. Mass Spectrom., 11, p. 1275Sparrapan, R., Mendes, M.A., Eberlin, M.N., (2000) J. Mass Spectrom., 35, p. 189Meurer, E.C., Eberlin, M.N., J. Mass Spectrom., , in pressMoraes, L.A.B., Eberlin, M.N., (2001) J. Am. Soc. Mass Spectrom., 12, p. 150Moraes, L.A.B., Eberlin, M.N., (1997) J. Chem. Soc., Perkin Trans., 2, p. 210
Gas-phase Chemistry Of Acylium Ions, Seven-to-five Ring Contraction Of 1,3-dioxepane And 1,3-dioxep-5-ene
No full textAs shown by pentaquadrupole triple-stage mass spectrometric and 18O-labeling experiments, two seven-membered cyclic acetals, 1,3-dioxepane and 1,3-dioxep-5-ene, fail to react by transacetalization with the gaseous acylium ions CH3C+=O and (CH3)2NC+=O. Instead, a novel and less exothermic but more kinetically favored reaction, seven-to-five ring contraction, occurs predominantly, and to great extents with the most reactive acylium ion, (CH3)2NC+=O. 1,3-Dioxepane yields O-acylated tetrahydrofurans; 1,3-dioxep-5-ene yields O-acylated 2,5-dihydrofurans.346670676Olah, G.A., Gramain, A., White, A.M., (1976) Carbonium Ions, 5, p. 2084. , edited by G. A. Olah and P. von R. Schleyer, Chapt. 35, Wiley-Interscience, New YorkGozzo, F.C., Sorrilha, A.E.P.M., Eberlin, M.N., (1996) J. Chem. Soc., Perkin Trans., 2, p. 587Moraes, L.A.B., Eberlin, M.N., (1997) J. Chem. Soc., Perkin Trans., 2, p. 2105Chatfield, D.A., Bursey, M.M., (1976) J. Am. Chem. Soc., 98, p. 6492Staley, R.H., Wieting, R.D., Beauchamp, J.L., (1977) J. Am. Chem. Soc., 99, p. 5964Kumakura, M., Sigiura, T., (1978) J. Phys. Chem., 82, p. 639Sparapani, C., Speranza, M., (1980) J. Am. Chem. Soc., 102, p. 3120Kim, J.K., Caserio, M.C., (1982) J. Am. Chem. Soc., 104, p. 4624Attinà, M., Cacace, F., (1983) J. Am. Chem. Soc., 105, p. 1122Caserio, M.C., Kim, J.K., (1983) J. Am. Chem. Soc., 105, p. 6896Paradisi, C., Kenttämaa, H.I., Le, Q.T., Caserio, M.C., (1988) Org. Mass Spectrom., 23, p. 521Rahman, N.A., Fisher, C.L., Caserio, M.C., (1988) Org. Mass Spectrom., 23, p. 517Kotiaho, T., Eberlin, M.N., Shay, B.J., Cooks, R.G., (1993) J. Am. Chem. Soc., 115, p. 1004Creaser, C.S., Wiliamson, B.L., (1996) J. Chem. Soc., Perkin Trans., 2, p. 427Eberlin, M.N., Majumdar, T.K., Cooks, R.G., (1992) J. Am. Chem. Soc., 114, p. 2884Eberlin, M.N., Cooks, R.G., (1993) J. Am. Chem. Soc., 115, p. 9226Eberlin, M.N., Cooks, R.G., (1993) Org. Mass Spectrom., 28, p. 679Moraes, L.A.B., Gozzo, F.C., Eberlin, M.N., Vainiotalo, P., (1997) J. Org. Chem., 62, p. 5096Carvalho, M.C., Moraes, L.A.B., Kascheres, C., Eberlin, M.N., (1997) J. Mass Spectrom., 32, p. 1137Carvalho, M.C., Juliano, V.F., Kascheres, C., Eberlin, M.N., (1997) J. Chem. Soc., Perkin Trans., 2, p. 2347Moraes, L.A.B.M., Eberlin, M.N., (1998) J. Am. Chem. Soc., 120, p. 11136Wang, F., Ma, S., Andy Tao, W., Cooks, R.G., (1999) Angew. Chem. Int. Ed., 38, p. 386Wang, F., Tao, W.A., Cooks, R.G., Gozzo, F.C., Eberlin, M.N., (1999) J. Org. Chem., 64, p. 3213Moraes, L.A.B., Pimpim, R.S., Eberlin, M.N., (1996) J. Org. Chem., 61, p. 8726Moraes, L.A.B., Eberlin, M.N., J. Am. Chem. Soc., , submitted for publicationMeerwein, H., (1955) Angew. Chem., 67, p. 374Juliano, V., Kascheres, C., Gozzo, F.C., Eberlin, M.N., Lago, C.L., (1996) Anal. Chem., 68, p. 1328Eberlin, M.N., (1997) Mass Spectrom. Rev., 16, p. 113Tiernan, T.O., Futrell, J.H., (1968) J. Phys. Chem., 72, p. 3080Schwartz, J.C., Wade, A.P., Enke, C.G., Cooks, R.G., (1990) Anal. Chem., 62, p. 1809Gill, P.M.W., Johnson, B.G., Pople, J.A., (1992) Chem. Phys. Lett., 197, p. 49
Triple-stage Pentaquadrupole (qqqqq) Mass Spectrometry And Ion/molecule Reactions
No full textThe general concepts, advantages, and applications of pentaquadrupole mass spectrometry and of a variety of pentaquadrupole multidimensional triple-stage (MS3) scans as applied to the study of gas-phase ion/molecule reactions are reviewed. An overview is presented of the development and the present stage of triple-stage pentaquadrupole mass spectrometry, and examples of successful applications of "QqQqQ-MS" in revealing, elucidating, and helping to consolidate new classes of gas-phase ion/molecule reactions are summarized. The variety of features and advantages that make pentaquadrupoles most suitable laboratories for studies of ion/molecule reactions, and the exceptional gains in chemical information and selectivity of QqQqQ-MS are also discussed. © 1997 John Wiley & Sons, Inc.163113144Augusti, R., Eberlin, M.N., Gas phase polar [4+ + 2] Diels-Alder cycloaddition reactions studied by multiple stage (MS2 and MS3) mass spectrometry (1994) The 13th International Mass Spectrometry Conference, p. 328. , BudapesteBakhtiar, R., Drader, J.J., Jacobson, D.B., Direct formation of cyclobutadiene radical cation from cis-3,4-dichloro-cyclobutene (1993) Org. Mass Spectrom., 28, p. 797Beaugrand, C., Devant, G., Nermag, S.N., Rolando, C., Jaouen, D., A multiquad triple analyzer MS/MS/MS (1986) Proc. 34th ASMS Conf. Mass Spectrom. and Allied Topics, p. 220. , Cincinnati, OHBeaugrand, C., Jaouen, D., Mestdagh, H., Rolando, C., Ion confinement in the collision cell of a multiquadrupole mass spectrometer: Access to chemical equilibrium and determination of kinetic and thermodynamic parameters of an ion-molecule reaction (1989) Anal. Chem., 61, p. 1447Bortolini, O., Yang, S.S., Cooks, R.G., Electrophilic bromination of gaseous aromatic compounds: Mechanism and linear free energy effects on reaction rates (1993) Org. Mass Spectrom., 28, p. 1313Bowers, M.T., (1979) Gas Phase Ion/Molecule Reactions, 1-3. , Academic Press: New YorkBurinsky, D.J., Cooks, R.G., Chess, E.K., Gross, M.L., Consecutive reactions in triple analyzer mass spectrometry and applications to mixture analysis (1982) Anal. Chem., 54, p. 295Busch, K.L., Glish, G.L., McLuckey, S.A., (1988) Mass Spectrometry/Mass Spectrometry: Techniques and Applications of Tandem Mass Spectrometry, , VCH: New YorkCarvalho, M.C., Eberlin, M.N., Kascheres, C., (1996) 19th Conference of the Brazilian Chemical SocietyCarvalho, M., Gozzo, F.C., Moraes, L.A.B., Mendes, M.A., Sparrapan, R., Kascheres, C., Eberlin, M.N., Locating the Charge Site of Heteroaromatic Cations, Chemistry, , to appearCarvalho, M.C., Juliano, V.F., Kascheres, C., Eberlin, M.N., Gas phase chemistry of the heterocumulene cations O=C=N+=C=O and O=C=C=N+O (1997) J. Chem. Soc. Perkin Trans. 2, p. 2347Carvalho, M.C., Moraes, L.A.B., Kascheres, C., Eberlin, M.N., On the structure of the mlz 70 ions from (N - H)-succinimide and N-bromo succinimide. O=C=N+= C=O? (1997) J. Mass Spectrom., 10, p. 1137Cody, R.B., Burnier, R.C., Cassady, C.J., Freiser, B.S., Consecutive collision-induced dissociations in Fourier transform mass spectrometry (1982) Anal. Chem., 54, p. 2225Cooks, R.G., Beynon, J.H., Caprioli, R.M., Lester, G.R., (1973) Metastable Ions, , Elsevier: AmsterdamCooks, R.G., Hoke II, S.H., Morand, K.L., Lammert, S.A., Mass spectrometers: Instrumentation (1992) Int. J. Mass Spectrom. Ion Proc., 118-119, p. 1Cooks, R.G., Patrick, S., Kotiaho, T., McLuckey, S.A., Thermochemical determination by the kinetic method (1994) Mass Spectrom. Rev., 13, p. 287Dempster, A., (1931) J. Phil. Mag., 31, p. 438Dolnikowski, G.G., Heath, T.G., Watson, J.T., Scrivens, J.H., Rolando, C.H., A study of the gas-phase reaction between protonated acetaldehyde and methanol (1990) J. Am. Chem. Soc., 1, p. 481Eberlin, M.N., Cooks, R.G., Polar [4 + 2+] Diels-Alder cycloadditions of acylium ions in the gas phase (1993) J. Am. Chem. Soc., 115, p. 9226Eberlin, M.N., Cooks, R.G., Gas-phase oxirane addition to acylium ions on reaction with 1,3-dioxolanes elucidated by tandem and triple stage mass spectrometric experiments (1993) Org. Mass Spectrom., 28, p. 679Eberlin, M.N., Kotiaho, T., Shay, B.J., Yang, S.S., Cooks, R.G., Gas-phase Cl+ affinities of pyridines determined by the kinetic method using multiple stage (MS3) mass spectrometry (1994) J. Am. Chem. Soc., 116, p. 2457Eberlin, M.N., Majumdar, T.K., Cooks, R.G., Structures and mechanisms of reactions of isomeric C2H3O+ and C2H3S+ ions revealed through ion/molecule reactions in conjunction with 2D and 3D mass spectrometry (1992) J. Am. Chem. Soc., 114, p. 2884Eberlin, M.N., Morgon, N.H., Yang, S.S., Shay, B.J., Cooks, R.G., Polar [4 + 2+] Diels-Alder cycloaddition to nitrilium and immonium ions in the gas phase: Applications of multiple stage mass spectrometry in a pentaquadrupole instrument (1995) J. Am. Soc. Mass Spectrom., 6, p. 1Eberlin, M.N., Sorrilha, A.E.P.M., Gozzo, F.C., Pimpim, R.S., A novel [3 + 2] 1,3-cycloaddition of the ionized carbonyl ylide +CH2 - O - CH2 • with carbonyl compounds in the gas phase (1997) J. Am. Chem. Soc., 119, p. 3550Eberlin, M.N., Sparrapan, R., Gozzo, F.C., Nogueira, J.C., Santos, C., Oxygen atom transfer to SFn + in the gas phase J. Am. Soc. Mass. Spectrom., , to appearEgsgaard, H., Carlsen, L., The C2H3O+ chemi-ion - Acetyl cation or O-protonated ketene? (1995) Chem. Phys. Letters, 225, p. 78Egsgaard, H., Carlsen, L., Sorrilha, A.E.P.M., Eberlin, M.N., Intermediates in the sulphur-rich flames. on the identity of the C2H3S+ chemi-ion (1996) Proceedings of the 44nd ASMS Conference on Mass Spectrometry and Allied Topics, p. 452Eller, K., Schwarz, H., Organometallic chemistry in the gas phase (1991) Chem. Rev., 91, p. 1121Eyring, H., Hirschfelder, J.O., Taylor, H.S., The theoretical treatment of chemical reactions produced by ionization processes (1936) J. Chem. Phys., 4, p. 479Farrar, J.M., Saunders, W.H., (1988) Techniques for the Study of Ion-Molecule Reactions, , Wiley: New YorkFetterolf, D.D., Yost, R.A., Eyler, J.R., The use of reactive collisions in tandem mass spectrometry for the differentiation of isomer structures (1984) Org. Mass Spectrom., 19, p. 104Franklin, J.L., (1972) Ion-Molecule Reactions, Spectrometry, , Plenum Press: New YorkFutrell, J.H., (1986) Gaseous Ion Chemistry and Mass Spectrometry, , Wiley: New YorkGozzo, F.C., Eberlin, M.N., The isomers of ionized dimethyl sulfoxide (C2H6OS+•) and their CH3OS+ fragments. An ab initio and multiple stage mass spectrometric study (1995) J. Mass Spectrom., 30, p. 1553Gozzo, F.C., Eberlin, M.N., The ionized methylene transfer from the distonic radical cation +CH2 - O - CH2 • to heterocyclic compounds. A pentaquadrupole mass spectrometry study (1995) J. Am. Soc. Mass Spectrom., 6, p. 554Gozzo, F.C., Mendes, M.A., Sparrapan, R., Eberlin, M.N., Azabenzynium ions: Stable hetarynium ions and reactive dienophiles in polar [4+2+] cycloadditions in the gas phase J. Am. Chem. Soc., , to appearGozzo, F.C., Sorrilha, A.E.P.M., Eberlin, M.N., The generation, stability, dissociation and ion/molecule chemistry of sulfinyl cations in the gas phase (1996) J. Chem. Soc. Perkin Trans. 2, p. 587Grant, E.R., Cooks, R.G., Mass spectrometry and its use in tandem with laser spectroscopy (1990) Science, 250, p. 61Graul, S.T., Squires, R.R., Advances in flow reaction techniques for the study of gas-phase ion chemistry (1988) Mass Spectrom. Rev., 7, p. 263Graul, S.T., Squires, R.R., Gas-phase acidities derived from threshold energies for activated reactions (1990) J. Am. Chem. Soc., 112, p. 2517Gross, M.L., Mass spectrometry research: An interplay between ion chemistry, instrumental development, and application (1989) Mass Spectrom. Rev., 8, p. 165Hammerum, S., Distonic radical cations in gaseous and condensed phase (1988) Mass Spectrom. Rev., 7, p. 123Harrison, A.G., (1983) Chemical Ionization Mass Spectrometry, , CRC Press: Boca RatonHeath, T.G., Allison, J., Watson, J.T., Selective detection of the tolyl cation among other [C7H7]+ isomers by ion/ molecule reaction with dimethyl ether (1991) J. Am. Soc. Mass Spectrom., 2, p. 270Hippie, J.A., Condon, E.U., (1945) Phys. Rev., 68, p. 54Hollis, J., Tedder, J.M., Stewart Walker, G., Investigations of halonium ions in the gas phase (1991) J. Chem. Soc. Perkin Trans. 2, p. 1187Holmes, J.L., Assigning structures to ions in the gas phase (1985) Org. Mass Spectrom., 20, p. 169Jalonen, J., Application of reaction collisions for differentiation of isomeric organic ions in the gas phase (1985) J. Chem. Soc. Chem. Commun., p. 872Jennings, K., RConsecutive metastable transitions in a double-focusing mass spectrometer (1966) Chem. Commun., p. 283Juliano, V., (1996) FControl, Acquisition and Data Processing for Pentaquadrupole Sequential Mass Spectrometry, , Doctoral Thesis, State University of CampinasJuliano, V.F., Gozzo, F.C., Eberlin, M.N., Kascheres, C., Lago, C.L., Fast multidimensional (3D and 4D) MS2 and MS3 scans in a high-transmission pentaquadrupole mass spectrometer (1996) Anal. Chem., 68, p. 1328Kenttämaa, H.I., Cooks, R.G., Identification of protonated β-hydroxycarbonyl compounds by reactive collisions in tandem mass spectrometry (1989) J. Am. Chem. Soc., 111, p. 4122Kinter, M.T., Bursey, M.M., Ion/molecule reaction of ammonia with two translationally excited C2H5O+ isomers (1986) J. Am. Chem. Soc., 108, p. 1797Kotiaho, T., Shay, B.J., Cooks, R.G., Eberlin, M.N., Electrophilic aromatic Cl+ addition and CO+• substitution in the gas phase (1993) J. Am. Chem. Soc., 115, p. 1004Kruger, T.L., Litton, J.F., Kondrat, R.W., Cooks, R.G., Mixture Analysis by Mass-Analyzed Ion Kinetic Energy Spectrometry (1976) Anal. Chem., 48, p. 2113Leinonen, A., Vainiotalo, P., Chemical ionization mass spectra of simple 1,3-dioxolanes and their sulphur analogues recorded with methane, isobutane, ammonia and acetone as Reagent gas (1994) Org. Mass Spectrom., 29, p. 295Levsen, K., Schwarz, H., Gas phase chemistry of collisionally activated ions (1983) Mass Spectrom. Rev., 2, p. 77Lu, L., Yang, S.S., Wang, Z., Cooks, R.G., Eberlin, M.N., Normal and inverse electron demand Diels-Alder cycloaddition of protonated and methylated carbonyl compounds in the gas phase (1995) J. Mass Spectrom., 30, p. 581Ma, S., Wong, P., Yang, S.S., Cooks, R.G., Gas-phase molecular, molecular pair, and molecular triplet Fe+ affinities of pyridines (1996) J. Am. Chem. Soc., 118, p. 6010Ma, S., Wong, P., Cooks, R.G., Gozzo, P.C., Eberlin, M.N., Stereoelectronic effects in phosphorous dichloride cation/pyridine complexes (1997) Int. J. Mass. Spectrom. Ion Processes, 163, p. 89Majumdar, T.K., Eberlin, M.N., Cooks, R.G., Green, M.M., Muñoz, B., Reidy, M.P., Structural studies on alkylisocyanate polymers by thermal degradation tandem mass spectrometry (1991) J. Am. Soc. Mass Spectrom., 2, p. 130McGilvery, D.C., Morrison, J.D., A mass spectrometer for the study of laser-induced photodissociation of ions (1978) Int. J. Mass Spectrom. Ion Phys., 28, p. 81McLafferty, F.W., (1983) Tandem Mass SpectrometryWiley: New YorkMcLukey, S.A., Sallans, L., Cody, R.B., Burnier, R.C., Verma, S., Freiser, B.S., Cooks, R.G., Energy-resolved tandem and Fourier-transform mass spectrometry (1982) Int. J. Mass Spectrom. Ion Phys., 44, p. 215Mendes, M.A., Moraes, L.A.B., Pimpim, R.S., Kostiainen, R., Kotiaho, T., Eberlin, M.N., A novel oxygen atom transfer reaction of ozone to ionized pyridine, pyrimidine, methyl halides and halogen atoms in the gas phase J. Org. Chem., , to appearMestdagh, H., Rolando, C., Metal-promoted carbon-carbon bond formation in the gas phase: Reaction of iron carbonyl cations with allyl chloride (1989) J. Am. Chem. Soc., 111, p. 3476Moraes, L.A.B., Eberlin, M.N., to appear (a)Moraes, L.A.B., Eberlin, M.N., to appear (b)Moraes, L.A.B., Eberlin, M.N., Transacetalization of 1,3-dioxane with acylium and sulfinyl cations in the gas phase (1997) J. Chem. Soc. Perkin Trans. 2, p. 2105Moraes, L.A.B., Eberlin, M.N., Ring expansion of epoxides and homologues upon acylation with acylium ions in the gas phase J. Org. Chem., , to appear (c)Moraes, L.A.B., Gozzo, F.C., Eberlin, M.N., Vainiotalo, Transacetalization with acylium ions. A structurally diagnostic ion-molecule reaction for cyclic acetals and ketals in the gas phase (1997) J. Org. Chem., 62, p. 5096Moraes, L.A.B., Pimpim, R.S., Eberlin, M.N., Novel ketalization reaction of acylium ions with diols and analogues in the gas phase (1996) J. Org. Chem., 61, p. 8726Morrison, J.D., Stanney, K., Tedder, J.M., The reactions of some common electrophiles, CH3 +, NO+, NO2 ++, and O2NCH2 +, with monosubstituted benzenes in the gas phase (1981) J. Chem. Soc. Perkin Trans. 2, p. 967Morrison, J.D., Stanney, D.A., Tedder, J., The design and development of a quinquequadrupole mass spectrometer (1986) Proc. 34th ASMS Conf. Mass Spectrom. and Allied Topics, p. 222. , Cincinnati, OHMunson, M.S.B., Field, F.H., Chemical ionization mass spectrometry I. General introduction (1966) J. Am. Chem. Soc., 88, p. 2621O'Lear, J.R., Wright, L.G., Louris, J.N., Cooks, R.G., The reaction intermediate spectrum: A new type of experiment in tandem mass spectrometry (1987) Org. Mass Spectrom., 22, p. 348Paradisi, C., Kenttämaa, H., Le, Q.T., Caserio, M.C., Gas-phase ion-molecule reactions of thioic and dithioic acid derivatives. Condensation reaction with alkenes and alkynes (1988) Org. Mass Spectrom., 23, p. 521Pimpim, R.S., Sorrilha, A.E.P.M., Eberlin, M.N., (1996) The 18th Brazilian Chemical Society MeetingRanasinghe, A., Cooks, R.G., Sethi, S.K., Selective isotopic exchange of polyfunctional ions in tandem mass spectrometry: Methodology, applications and mechanism (1992) Org. Mass Spectrom., 27, p. 77Sablier, M., Reactions of gas-phase transition metal cations with cyanogen bromine and cyanogen iodide (1994) The 13th International Mass Spectrometry Conference, p. 232. , BudapesteSablier, M., Capron, L., Mestdagh, H., Rolando, C., Gas-phase reactivity of transition metal cations with cyanogen radical precursors (1994) Tetrahedron Letters, 35, p. 2895Schoen, A.E., Amy, J.W., Ciupek, J.D., Cooks, R.G., Dobberstein, P., Jung, G., A hybrid BEQQ mass spectrometer (1985) Int. J. Mass Spectrom. Ion Proc., 65, p. 125Schwartz, J.C., Schey, K.L., Cooks, R.G., A pentaquadrupole instrument for reaction intermediate scans and other MS-MS-MS experiments (1990) Int. J. Mass Spectrom. Ion Processes, 101, p. 1Schwartz, J.C., Wade, A.P., Enke, C.G., Cooks, R.G., Systematic delineation of scan modes in multidimensional mass spectrometry (1990) Anal. Chem., 62, p. 1809Shay, B.J., Eberlin, M.N., Cooks, R.G., Wesdemiotis, C., Ion-molecule reactions and collision-activated dissociation of C4H4 +• isomers: A case study in the use of the MS3 capabilities of a pentaquadrupole mass spectrometer (1992) J. Am. Soc. Mass Spectrom., 3, p. 518Smyth, H.D., Products and processes of ionization by low speed electrons (1931) Rev. Mod. Phys., 3, pp. 347-391Sorrilha, A.E.P.M., Gozzo, F.C., Eberlin, M.N., Polar [4 + 2+] Diels-Alder cycloaddition reactions of heterodienes. An on-line multiple stage (MS2 and MS3) mass spectrometric study (1994) The 13th International Mass Spectrometry Conference, p. 329. , BudapesteSorrilha, A.E.P.M., Gozzo, F.C., Pimpim, R.S., Eberlin, M.N., Multiple stage pentaquadrupole mass spectrometry for generation and characterization of gas-phase ionic species. The case of the PyC2H+• isomers (1996) J. Am. Soc. Mass Spectrom., 7, p. 1126Sparrapan, R., Moraes, L.A.B., Gozzo, F.C., Eberlin, M.N., Augusti, R., Polar [4+ + 2] cycloaddition of protonated 1-aza and 2-azabutadiene in the gas phase J. Org. Chem., , to appearTalrose, V.L., (1952) Dokl. Akad. Nauk SSR, 86, pp. 909-921Tedder, J.M., Walker, G.S., Investigation of oxonium ions (1991) J. Chem. Soc. Perkin Trans. 2, p. 317Thomson, J.J., (1913) Rays of Positive Electricity and Their Applications in Chemical Analysis, , Longmans, Green and Co.: New YorkTurecek, F., Hanus, V., Retro-Diels Alder reaction in mass spectrometry (1984) Mass Spectrom. Rev., 3, p. 85Vainiotalo, P., Moraes, L.A., Eberlin, M.N., A gas phase structurally diagnostic ion/molecule reaction for 1,3-O,O and 1,3-O,S-heterocycles (1996) Proceedings of the 44th ASMS Conference on Mass Spectrometry and Allied Topics, p. 453Vestal, M.L., Futrell, J.H., Photodissociation of CH3Cl+ and CH3Br+ in a tandem quadrupole mass spectrometry (1974) Chem. Phys. Lett., 28, p. 559Wong, P.S.H., Ma, S., Yang, S.S., Gozzo, F.C., Eberlin, M.N., Sulfur trifluoride cation (SF3 +) affinities of pyridines determined by the kinetic method: Stereoelectronic effects in the gas phase (1997) J. Am. Chem. Soc., 8, p. 68Yang, S.S., Bortolini, O., Steinmetz, A., Cooks, R.G., Relative cyanide cation (+CN) affinities of pyridines determined by the kinetic method using multiple stage (MS3) mass spectrometry (1995) J. Mass Spectrom., 30, p. 184Yang, S.S., Chen, G., Ma, S., Cooks, R.G., Gozzo, F.C., Eberlin, M.N., Relative carbonyl isocyanate cation [OCNCO]+ affinities of pyridines determined by the kinetic method using multiple stage (MS3) mass spectrometry (1995) J. Mass Spectrom., 30, p. 807Yang, S.S., Wong, P., Ma, S., Cooks, R.G., SiCl3" and SiCl+ affinities for pyridines determined by using the kinetic method with multiple stage mass spectrometry: Agostic effects the gas phase (1996) J. Am. Soc. Mass Spectrom., 7, p. 198Yost, R.A., Enke, C.G., Selected ion fragmentation with a tandem quadrupole mass spectrometer (1978) J. Am. Chem. Soc., 100, p. 2274Yost, R.A., Enke, C.G., (1983) Tandem Quadrupole Mass Spectrometry, , McLafferty, F. W., Ed.Wiley: New YorkYu, T.Y., Cheng, T.M.H., Kempter, V., Lampe, F.W., Ionic reactions in monosilane. Some radiation chemistry implications (1972) J. Phys. Chem., 76, p. 3321Zhang, M.Y., Wesdemiotis, C., Marchetti, M., Danis, P.O., Ray Jr., J.C., Carpenter, B.K., McLafferty, F.W., Characterization of four C4H4 molecules and cations by neutralization-reionization mass spectrometry (1989) J. Am. Chem. Soc., 111, p. 834
Reactions Of Gaseous Acylium Ions With 1,3-dienes: Further Evidence For Polar [4 + 2+] Diels-alder Cycloaddition
No full textA novel reaction of acylium and thioacylium ions, polar [4 + 2+] Diels-Alder cycloaddition with 1,3-dienes and O-heterodienes, has been systematically investigated in the gas phase (Eberlin MN, Cooks RG. J. Am. Chem. Soc. 1993; 115: 9226). This polar cycloaddition, yet without precedent in solution, likely forms cyclic 2,5-dihydropyrylium ions. Here we report the reactions of gaseous acylium ions [(CH3)2N-C+=O, Ph-C+=O, (CH3)2N-C+=S, CH3-C+=O, CH3CH2-C+=O, and CH2=CH-C+=O] with several 1-oxy-substituted 1,3-dienes of the general formula RO-CH=CH-C(R1)=CH2, which were performed to collect further evidence for cycloaddition. In reactions with 1-methoxy and 1-(trimethylsilyloxy)1,3-butadiene, adducts are formed to a great extent, but upon collision activation they mainly undergo structurally unspecific retro-addition dissociation. In reactions with Danishefsky's diene (trans-1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene), adducts are also formed to great extents, but retro-addition is no longer their major dissociation; the ions dissociate instead mainly to a common fragment, the methoxyacryl cation of m/z 85. This fragment ion is most likely formed with the intermediacy of the acyclic adduct, which isomerizes prior to dissociation by a trimethylsilyl cation shift. Theoretical calculations predict that meta cycloadducts bearing 1-methoxy and 1-trimethylsilyloxy substituents are unstable, undergoing barrierless ring opening induced by the charge-stabilizing effect of the 1-oxy substituents. In contrast, for the reactions with 1-acetoxy-1,3-butadiene, both the experimental results and theoretical calculations point to the formation of intrinsically stable cycloadducts, but the intact cycloadducts are either not observed or observed in low abundances. Both the isomeric ortho and meta cycloadducts are likely formed, but the nascent ions dissociate to great extents owing to excess internal energy. The ortho cycloadducts dissociate by ketene loss; the meta cycloadducts undergo intramolecular proton transfer to the acetoxy group followed by dissociation by acetic acid loss to yield aromatic pyrylium ions. Either or both of these dissociations, ketene and/or acetic acid loss, dominate over the otherwise favored retro-Diels-Alder alternative. The pyrylium ion products therefore constitute compelling evidence for polar [4 + 2+] cycloaddition since their formation can only be rationalized with the intermediacy of cyclic adducts. Copyright © 2003 John Wiley & Sons, Ltd.383305314Boger, D.L., Weinreb, S.N., (1987) Hetero Diels-Alder Methodology in Organic Synthesis, , Wasserman HH (ed.). Academic Press: New YorkCarruthers, W., (1990) Cycloaddition Reactions in Organic Synthesis, , Pergamon Press: OxfordTietze, L.F., Kettschau, G., (1997) Top. Curr. Chem., 189, p. 1Fleming, I., (1998) Pericyclic Reactions, , Wiley: OxfordMachat, R., Schmidt, R.R., (1970) Angew. Chem., Int. Ed. Engl., 9, p. 31Schmidt, R.R., (1973) Angew. Chem., Int. Ed. Engl., 12, p. 212Shimizu, H., Araki, N., Muraoka, O., Tanabe, G., (1996) Chem. Commun., p. 2185Brodbelt, J.S., (1997) Mass Spectrom. Rev., 16, p. 91Green, M.K., Lebrilla, C.B., (1997) Mass Spectrom. Rev., 16, p. 53Eberlin, M.N., (1997) Mass Spectrom. Rev., 16, p. 113Filippi, A., Giardini, A., Piccirillo, S., Speranza, M., (2000) Int. J. Mass Spectrom., 198, p. 137Gronert, S., (2001) Chem. Rev., 101, p. 329Nibbering, N.M.M., (2000) Int. J. Mass Spectrom., 200, p. 27Takashima, K., Riveros, J.M., (1998) Mass Spectrom. Rev., 17, p. 409Turecek, F., Wolken, J.K., (2001) J. Phys. Chem. A, 105, p. 8740Moraes, L.A.B., Eberlin, M.N., Laali, K.K., (2001) Organometallics, 20, p. 4863Petucci, C., Guler, L., Kenttamaa, H.I., (2002) J. Am. Soc. Mass Spectrom., 13, p. 362Denault, J.W., Wang, F., Cooks, R.G., Gozzo, F.C., Eberlin, M.N., (2000) J. Phys. Chem. A, 104, p. 11290Gozzo, F.C., Moraes, L.A.B., Eberlin, M.N., Laali, K.K., (2000) J. Am. Chem. Soc., 122, p. 7776Wincel, H., Fokkens, R.H., Nibbering, N.M.M., (2000) Rapid Commun. Mass Spectrom., 14, p. 135Luna, A., Amekraz, B., Morizur, J.P., Tortajada, J., Mo, O., Yanez, M., (2000) J. Phys. Chem. A, 104, p. 3132D'Oca, M.G.M., Moraes, L.A.B., Pilli, R.A., Eberlin, M.N., (2001) J. Org. Chem., 66, p. 3854Kretzschmar, I., Schroder, D., Schwarz, H., Rue, C., Armentrout, P.B., (2000) J. Phys. Chem. A, 104, p. 5046O'Hair, R.A.J., (2002) Chem. Commun., p. 20Gronert, S., Huang, R., (2001) J. Am. Chem. Soc., 123, p. 8606Grandinetti, F., Pepi, F., Ricci, A., (1996) Chem. Eur. J., 2, p. 495Moraes, L.A.B., Gozzo, F.C., Eberlin, M.N., Vainiotalo, P., (1997) J. Org. Chem., 62, p. 5096Creaser, C.S., Williamson, B.L., (1998) Eur. Mass Spectrom., 4, p. 103Sharifi, M., Einhorn, J., (1999) Int. J. Mass Spectrom., 190-191, p. 253Grützmacher, H.F., Dohmeier-Fischer, S., (1998) Int. J. Mass Spectrom. Ion. Processes, 179-180, p. 207Moraes, L.A.B., Eberlin, M.N., (1998) J. Am. Chem. Soc., 120, p. 11136Reid, G.E., Tichy, S.E., Pérez, J., O'Hair, R.A.J., Simpson, R.J., Kenttämaa, H.I., (2001) J. Am. Chem. Soc., 123, p. 1184Meurer, E.C., Moraes, L.A.B., Eberlin, M.N., (2001) Int. J. Mass Spectrom., 212, p. 445Moraes, L.A.B., Eberlin, M.N., (2002) J. Mass Spectrom., 37, p. 162Colorado, A., Barket, D.J., Hurst, J.M., Shepson, J.B., (1998) Anal. Chem., 70, p. 5129Sparrapan, R., Mendes, M.A., Carvalho, M., Eberlin, M.N., (2000) Chem. Eur. J., 6, p. 321Eberlin, M.N., Sorrilha, A.E.P.M., Gozzo, F.C., Pimpim, R.S., (1997) J. Am. Chem. Soc., 119, p. 3550Gevrey, S., Taphanel, M.H., Morizur, J.P., (1998) J. Mass. Spectrom., 33, p. 399Bouchoux, G., Nguyen, M.T., Salpin, J.Y., (2000) J. Phys. Chem., 104, p. 5778Augusti, R., Gozzo, F.C., Moraes, L.A.B., Sparrapan, R., Eberlin, M.N., (1998) J. Org. Chem., 63, p. 4889Meurer, E.C., Eberlin, M.N., (2001) Int. J. Mass Spectrom., 210 (211), p. 469Holman, R.W., Rozeboom, M.D., Gross, M.L., (1986) Tetrahedron, 42, p. 6235Heinrich, N., Koch, W., Morrow, J.C., Schwarz, H., (1988) J. Am. Chem. Soc., 110, p. 6332Eberlin, M.N., Cooks, R.G., (1993) J. Am. Chem. Soc., 115, p. 9226Eberlin, M.N., Majumdar, T.K., Cooks, R.G., (1992) J. Am. Chem. Soc., 114, p. 2884Carvalho, M.C., Juliano, V.F., Kascheres, C., Eberlin, M.N., (1997) J. Chem. Soc., Perkin Trans. 2, p. 2347Turecek, F., Hanus, V., (1984) Mass Spectrom. Rev., 3, p. 85Meurer, E.C., Eberlin, M.N., (2002) J. Mass Spectrom., 37, p. 146Juliano, V.F., Kascheres, C., Gozzo, F.C., Eberlin, M.N., Lago, C.L., (1996) Anal. Chem., 68, p. 1328Tiernan, T.O., Futrell, J.H., (1968) J. Phys. Chem., 72, p. 3080Moraes, L.A.B., Eberlin, M.N., (2001) J. Am. Soc. Mass Spectrom., 12, p. 150Fleming, I., (1976) Frontier Orbitals and Organic Chemical Reactions, , Wiley: New YorkMoraes, L.A.B., Eberlin, M.N., (1997) J. Chem. Soc., Perkin Trans. 2, p. 210
Gaseous Sf3 +: An Efficient Electrophilic Monofluorinating Agent For Five-membered Heteroaromatic Compounds
No full textReactions of gaseous SF3 + ions with furan, thiophene, pyrrole, and several of their alkyl derivatives were performed via MS2 experiments and found to occur readily both by electron abstraction and F+ transfer. Then, by performing MS3 experiments, the F+ transfer products - the protonated monofluorinated molecules - were mass-selected and deprotonated by a second reaction with a stronger base. F+ transfer from gaseous SF3 + followed by deprotonation promotes therefore C-H by C-F replacement in five-membered heteroaromatic compounds and the efficient gas-phase synthesis of their neutral monofluorinated derivatives.651339203925Liebman, J.F., Greenberg, A., Dolbier, W.R., (1988) Fluorine Containing Molecules: Structure, Reactivity, Synthesis and Applications, , VCH: New YorkWalker, S.B., (1989) Fluorine Compounds as Agrochemicals, , Fluorochem Limited: GlossopBanks, R.E., (1979) Organofluorine Chemicals and Their Industrial Applications, , Ellis Horwood: ChichesterKirk, K.L., (1991), 9 B. , Biochemistry of the Elements SeriesFrieden, E., Ed.Plenum Press: New YorkRozen, S., (1996) Acc. Chem. Res., 29, p. 243Wilkinson, J.A., (1992) Chem Rev., 92, p. 505Cartwright, M.M., Woolf, A.A., (1984) J. Fluorine Chem., 25, p. 263Cartwright, M.M., Woolf, A.A., (1981) J. Fluorine Chem., 19, p. 10Chrite, K.O., (1984) J. Fluorine Chem., 25, p. 269Chrite, K.O., (1983) J. Fluorine Chem., 22, p. 519Rozen, S., Gal, C., (1984) Tetrahedron Lett., 25, p. 449Rozen, S., Gal, C., (1988) J. Org. Chem., 53, p. 2803Hewitt, C.D., Silvester, M.J., (1988) Aldrichimica Acta, 21, p. 3Moissan, (1986) J. Fluorine Chem., p. 33Olah, G.A., Welch, J.T., Vankar, Y.D., Nojima, M., Kerekes, I., Olah, J.A., (1979) J. Org. Chem., 44, p. 3872Mascaretti, O., (1993) Aldrichimica Acta, 26, p. 47Burger, K., Helmreich, B., (1994) Heterocycles, 39, p. 819Qiu, Z., Burton, D.J., (1994) Tetrahedron Lett., 35, p. 4319Sham, H.L., Betebenner, D.A., (1991) J. Chem. Soc., Chem. Commun., p. 1135Shi, G., Sclosser, M., (1993) Tetrahedron, 49, p. 1445Kassmi, A.E., Fache, F., Lemaire, M., (1994) Synth. Commun., 24, p. 95Cerichelli, G., Crestoni, M.E., Fornarini, S., (1990) Gazz. Chim. Ital., 120, p. 749Moraes, L.A.B., Pimpim, R.S., Eberlin, M.N., (1996) J. Org. Chem., 61, p. 8726Moraes, L.A.B., Gozzo, F.C., Eberlin, M.N., Vainiotalo, P., (1997) J. Org. Chem., 62, p. 5096Brodbelt, J.S., (1997) Mass Spectrom. Rev., 16, p. 91Gozzo, F.C., Moraes, L.A.B., Sparrapan, R., Eberlin, M.N., (1998) J. Org. Chem., 63, p. 4889Chou, P.K., Thoen, K.K., Kenttämaa, H.I., (1998) J. Org. Chem., 63, p. 4470Williamson, B.L., Creaser, C.S., (1998) Eur. Mass Spectrom., 4, p. 103Gerbaux, P., Haverbeke, Y.V., Flammang, R., (1998) Int. J. Mass Spectrom., 184, p. 39Mendes, M.A., Moraes, L.A.B., Sparrapan, R., Eberlin, M.N., Kostiainen, R., Kotiaho, T., (1998) J. Am. Chem. Soc., 120, p. 7869Takashima, K., Riveros, J.M., (1998) Mass Spectrom. Rev., 17, p. 409Wang, F., Tao, W.A., Gozzo, F.C., Eberlin, M.N., Cooks, R.G., (1999) J. Org. Chem., 64, p. 3213Cacace, F., De Petris, G., Pepi, F., Rosi, M., Sgamellotti, A., (1999) Angew. Chem., Int. Ed., 38, p. 2408Sharifi, M., Einhorn, J., (1999) Int.J. Mass Spectrom., 190-191, p. 253Frank, A.J., Turecek, F., (1999) J. Phys. Chem. A, 103, p. 5348Brönstrup, M., Schröder, D., Schwarz, H., Organometallics (1999), 18, p. 1939Sparrapan, R., Mendes, M.A., Carvalho, M., Eberlin, M.N., (2000) Chem. Eur. J., 6, p. 321Moraes, L.A.B., Eberlin, M.N., (2000) Chem. Eur. J., 6, p. 897Dillard, J.G., Troester, J.H., (1975) J. Phys. Chem., 79, p. 2455Javahery, G., Becker, H., Korobov, M.V., Farber, M., Cooper, D., Bohme, D.K., (1994) Int. J. Mass Spectrom. Ion Proc., 133, p. 73Cipollini, R., Crestoni, M.E., Fornarini, S., (1997) J. Am. Chem. Soc., 119, p. 9499Grandinetti, F., Pepi, F., Ricci, A., (1996) Chem. Eur. J., 2, p. 495Aschi, M., Grandinetti, F., Vinciguerra, V., (1998) Chem. Eur. J., 4, p. 2366Sparrapan, R., Mendes, M.A., Ferreira, I.P.P., Eberlin, M.N., Santos, C., Nogueira, J.C., (1998) J. Phys. Chem. A, 102, p. 5189Sparrapan, R., Mendes, M.A., Eberlin, M.N., (1999) Int. J. Mass Spectrom. Ion Proc., 182-183, p. 369Wong, P.S.K., Ma, S., Yang, S.S., Cooks, R.G., Gozzo, F.C., Eberlin, M.N., (1997) J. Am. Soc. Mass Spectrom., 8, p. 68noteChriste, K.O., Dixon, D.A., (1992) J. Am. Chem Soc., 114, p. 2978Schwartz, J.C., Wade, A.P., Enke, C.G., Cooks, R.G., (1990) Anal. Chem., 62, p. 1809Eberlin, M.M., (1997) Mass Spectrom. Rev., 16, p. 113Juliano, V.F., Gozzo, F.C., Eberlin, M.N., Kascheres, C., Lago, C.L., (1996) Anal. Chem., 68, p. 1328Tiernan, T.O., Futrell, J.H., (1968) J. Phys. Chem., 72, p. 3080Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Pople, J.A., (1998), Gaussian 98, Revision A.6, Gaussian, Inc., Pittsburgh, PAMøller, C., Plesset, M.S., (1934) Phys. Rev., 46, p. 618Gill, P.M.W., Johnson, B.G., Pople, J.A., (1992) Chem. Phys. Lett., 197, p. 499Lee, C., Yang, W., Parr, R.G., (1988) Phys. Rev. B, 37, p. 785Becke, A.D., (1988) Phys. Rev. A, 38, p. 3098Schaftenaar, G., (1992) QCPE Bull., 12, p. 3. , http:// www.caos.kun.nl/~schaft/molden/molden.htmlBosshard, P., Eugster, C.H., (1966), 7, p. 377. , Advances in Heterocyclic ChemistryKatritzky,A.R., Boulton,A.J., Eds.Academic Press: New YorkGronowitz, S., (1963), 2, p. 1. , Advances in Heterocyclic ChemistryKatritzky,A.R., Ed.Academic Press: New YorkAlan Jones, R., (1970), 11, p. 384. , Advances in Heterocyclic ChemistryKatritzky,A.R., Boulton,A.J., Eds.Academic Press: New YorkHealth, T.G., Allison, J., Watson, J.T., (1991) J. Am. Chem. Soc., 2, p. 27
Analysis Of Street Ecstasy Tablets By Thin Layer Chromatography Coupled To Easy Ambient Sonic-spray Ionization Mass Spectrometry
No full textEcstasy is a famous illicit drug with varying drug composition, but it usually contains 3, 4-meth-ylenedioxymethamphetamine (MDMA) as the main active ingredient. The common proce-dure to identify ecstasy tablets uses testing kits, but its low specificity may lead to false posi-tives. Thin layer chromatography (TLC) is used worldwide in forensic investigations due to its simplicity, low-cost and versatility but may also lead to false positives. In this study, TLC sepa-ration of seven common ecstasy drugs: MDMA, metamphetamine, 3, 4-methylenedioxyeth-ylamphetamine (MDEA), 3, 4-methylenedioxyamphetamine (MDA), amphetamine, caffeine and lidocaine was attained, and twenty five apprehended street ecstasy tablets analyzed by TLC. Easy ambient sonic-spray ionization mass spectrometry (EASI-MS) was then performed directly on the surface of each TLC spot for MS characterization. The combination of TLC with EASI-MS is shown to provide a relatively simple and powerful screening tool for forensic analy-sis of street drugs with fast and indisputable results.15222227Renfroe, C.L., (1986) J. Psychoactive Drugs, 18, p. 363Jeffrey, W., (2004) Clarke's Analysis of Drugs and Poisons In Pharmaceuti-cals, Body Fluids and Postmortem Material, , Moffat, A.Osselton, M.Widdop, B.Galichet, L., eds.London, UK: Pharmaceutical PressSherlock, K., Wolff, K., Hay, A.W., Conner, M.J., (1999) Accid. Emerg. Med, 16, p. 194Sadeghipour, F., Veuthey, J.L.J., (1997) Chromatogr. A, 787, p. 137Bogusz, M.J.J., Chromatogr, B., (2000) Biomed. Sci. Appl, 748, p. 3Kato, N., Pharm, B., Fujita, S., Pharm, B., Ohta, H., Fukuba, M., Pharm, M., Hayakawa, K., (2008) J. Forensic Sci, 53, p. 1367Zakrzewska, A., Parczewski, A., Kazmierczak, D., Ciesielski, W., Kochanaa, J., (2007) Acta Chim. Slov, 54, p. 106Ifa, D.R., Wu, C., Ouyang, Z., Cooks, R., (2010) G. Analyst, 135, p. 669Alberici, R.M., Simas, R.C., Sanvido, G.B., Romão, W., Lalli, P.M., Benassi, M., Cunha, I.B.S., Eberlin, M.N., (2010) Anal Bioanal. Chem, , in pressHarris, G.A., Nyadong, L., Fernandez, F.M., (2008) Analyst, 133, p. 1297Chen, H., Gamez, G., Zenobi, R.J., (2009) Am. Soc. Mass Spectrom, 20, p. 1947Ifa, D.R., Gumaelius, L.M., Eberlin, L.S., Manicke, N.E., Cooks, R., (2007) G. Analyst, 132, p. 461Haddad, R., Sparrapan, R., Kotiaho, T., Eberlin, M.N., (2008) Anal Chem, 80, p. 898Santos, V.G., Regiani, T., Dias, F.F.G., Romão, W., Klitzke, C.F., Coelho, F., Eberlin, M.N., (2010) Angew. Chem. Int. Ed, , submitHaddad, R., Sparrapan, R., Eberlin, M.N., (2901) Rapid Commun. Mass Spectrom, 2006, p. 20Lalli, P.M., Sanvido, G.B., Garcia, J.S., Haddad, R., Cosso, R.G., Maia, D.R.J., Zacca, J.J., Eberlin, M., (2010) N. Analyst, 135, p. 745Haddad, R., Catharino, R.R., Marques, L.A., Eberlin, M.N., (2008) Rapid Commun. Mass Spectrom, 22, p. 3662Saraiva, S.S., Abdelnur, P.V., Catharino, R.R., Nunes, G., Eberlin, M.N., (2009) Rapid Commun. Mass Spectrom, 23, p. 357Abdelnur, P.V., Eberlin, L.S., Sá, G.F., Souza, S.V., Eberlin, M.N., (2008) Anal. Chem, 80, p. 7882Sawaya, A.C.H.F., Abdelnur, P.V., Eberlin, M.N., Kumazawa, S., Ahn, M.-R., Bang, K.-S., Nagaraja, N., Afrouzan, H., (2010) Talanta, 81, p. 100Saraiva, S.A., Abdelnur, P.V., Catharino, R.R., Nunes, G., Eberlin, M.N., (2009) Rapid Commun. Mass Spectrom, 23, p. 357Haddad, R., Sparrapan, R., Kotiaho, T., Eberlin, M.N., (2008) Anal. Chem, 80, p. 898Haddad, R., Milagre, H.M.S., Catharino, R.R., Eberlin, M.N., (2008) Anal. Chem, 80, pp. 2744-2750Eberlin, L.S., Abdelnur, P.V., Passero, A., de Sa, G.F., Daroda, R.J., de Souza, V., Eberlin, M.N., (2009) Analyst, 134, p. 1652Figueiredo, E.C., Sanvido, G.B., Arruda, M.A.Z., Eberlin, M.N., (2010) Analyst, 135, p. 726Gao, L., Cooks, R.G., Ouyang, Z., (2008) Anal. Chem, 80, p. 4026Syms, R., (2009) Anal. Bioanal. Chem, 393, pp. 427-42
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