Protomers: Formation, separation and characterization via travelling wave ion mobility mass spectrometry

Journal of Mass Spectrometry

Volumn 47, Issue 6, 2012, Pages 712-719

  Lalli, Priscila M ^a   Iglesias, Bernardo A ^b   Toma, Henrique E ^b   De Sa, Gilberto F ^c,d   Daroda, Romeu J ^c   Silva Filho, Juvenal C ^d   Szulejko, Jan E ^e   Araki, Koiti ^b   Eberlin, Marcos N ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c INSTITUTO NACIONAL DE METROLOGIA   (Brazil)

^d FEDERAL UNIVERSITY OF SERGIPE   (Brazil)

^e NONE   (United Kingdom)

Author keywords

Aniline; Electrospray ionization; Mass spectrometry, gas phase acidity, gas phase basicity; Protomers, protonation site; Pyridyl porphyrins; Travelling wave ion mobility

Indexed keywords

AMMONIA; ANILINE; DEPROTONATION; GASES; ION MOBILITY SPECTROMETERS; IONIZATION OF GASES; IONS; MASS SPECTROMETRY; PHASE EQUILIBRIA; PORPHYRINS; PROTONATION; SEPARATION; WAVE TRANSMISSION;

COLLISION INDUCED DISSOCIATION; GAS-PHASE ACIDITIES; ION MOBILITY; ION MOBILITY-MASS SPECTROMETRY; METHANOLIC SOLUTION; PROTONATION SITE; PYRIDYL; SEPARATION AND CHARACTERIZATIONS;

ELECTROSPRAY IONIZATION;

AMMONIA; ANILINE; POLYMER; PORPHYRIN;

ACIDITY; ALKALINITY; ARTICLE; DISSOCIATION; ELECTROSPRAY; GAS; ISOMER; ISOMERIZATION; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTOMER; PROTON TRANSPORT; SEPARATION TECHNIQUE; SOLVATION; TRAVELLING WAVE ION MOBILITY MASS SPECTROMETRY;

EID: 84862197553     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.2999     Document Type: Article

References (44)

1. + with HCN and protonation of CNP compounds. J. Phys. Chem. 1991, 95, 9864.
2. (b) K. A. Cox, S. J. Gaskell, M. Morris, A. Whiting. Role of the site of protonation in the low-energy decompositions of gas-phase peptide ions. J. Am. Soc. Mass Spectrorn. 1996, 7, 522.
3. (c) J. Graton, M. Berthelot, J.-F. Gal, S. Girard, C. Laurence, J. Lebreton, J.-Y. Le Questel, P.-C. Maria, P. Naus. Site of protonation of nicotine and nornicotine in the gas phase: pyridine or pyrrolidine nitrogen? J. Am. Chem. Soc. 2002, 124, 10552.
4. (d) O. Dopfer, N. Solca, J. Lemaire, P. Maitre, M.-E. Crestoni, S. Fornarini. Protonation sites of isolated fluorobenzene revealed by ir spectroscopy in the fingerprint range. J. Phys. Chem. A 2005, 109, 7881.
5. S. K. Pollack, J. L. Devlin, K. D. Summerhays, R. W. Taft, W. J. Hehre. The site of protonation in aniline. J. Am. Chem. Soc. 1977, 99, 4583.
6. Y. K. Lau, P. Kebarle. Substituent effects on intrinsic basicity of benzene - proton affinities of substituted benzenes. J. Am. Chem. Soc. 1976, 98, 7452.
7. (a) K. V. Wood, D. J. Burinsky, D. Cameron, R. G. Cooks. Site of gasphase cation attachment - protonation, methylation, and ethylation of aniline, phenol, and thiophenol. J. Org. Chem. 1983, 48, 5236.
8. (b) S. J. Pachuta, I. Isern-Flecha, R. G. Cooks. Charge stripping and the site of cationization of substituted aromatic-compounds. Org. Mass Spectrom. 1986, 21, 1.
9. Z. Karpas, Z. Berant, R. M. Stimac. An ion mobility spectrometry/mass spectrometry (IMS/MS) study of the site of protonation in anilines. Struct.Chem. 1990, 1, 201.
10. R. L. Smith, L. J. Chyall, B. J. Beasley, H. I. Kenttamaa. The site of protonation of aniline. J. Am. Chem. Soc. 1995, 117, 7971.
11. N. Russo, M. Toscano, A. Grand, T. Mineva. Proton affinity and protonation sites of aniline. Energetic behavior and density functional reactivity indices. J. Phys. Chem. A 2000, 104, 4017.
12. R. Flammang, N. Dechamps, L. Pascal, Y. Van Haverbeke, P. Berbaux, P. C. Nam, M. T. Nguyen. Ring versus nitrogen protonation of anilines. Org. Chem. Lett. 2004, 1, 23.
13. H. Borsdorf, G. Eiceman. Ion mobility spectrometry: Principles and applications. Appl. Spectros. Rev. 2006, 41, 323.
14. A. B. Kanu, P. Dwivedi, M. Tam, L. Matz, H. H. Hill. Ion mobility-mass spectrometry. J. Mass Spectrom. 2008, 43, 1-22.
15. (b) S. Armenta, M. Alcala, M. Blanco. A review of recent, unconventional applications of ion mobility spectrometry (IMS). Anal. Chim. Acta 2011, 703, 114.
16. (a) P. Dwivedi, C. Wu, L. M. Matz, B. H. Clowers, W. F. Siems, H. H. Hill. Gas-phase chiral separations by ion mobility spectrometry. Anal. Chem. 2006, 78, 8200.
17. (b) M. Benassi, Y. E. Corilo, D. Uria, R. Augusti, M. N. Eberlin. Recognition and resolution of isomeric alkyl anilines by mass spectrometry. J. Am. Soc. Mass Spectrom. 2009, 20, 269.
18. (c) M. Zhu, B. Bendiak, B. Clowers, H. H. Hill. Ion mobility-mass spectrometry analysis of isomeric carbohydrate precursor ions. Anal. Bioanal. Chem. 2009, 394, 1853.
19. S. Trimpin, D. E. Clemmer. Ion mobility spectrometry/mass spectrometry snapshots for assessing the molecular compositions of complex polymeric systems. Anal. Chem. 2008, 80, 9073.
20. F. A. Fernandez-Lima, C. Becker, A. M. McKenna, R. P. Rodgers, A. G. Marshall, D. H. Russell. Petroleum crude oil characterization by IMSMS and FTICR MS. Anal. Chem. 2009, 81, 9941.
21. E. R. Brocker, S. E. Anderson, B. H. Northrop, P. J. Stang, M. Bowers. Structures of metallosupramolecular coordination assemblies can be obtained by ion mobility spectrometry-mass spectrometry. J. Am. Chem. Soc. 2010, 132, 13486.
22. (a) G. Von Helden, T. Wyttenbach, M. T. Bowers. Conformation of macromolecules in the gas-phase - use of matrix-assisted laser-desorption methods in ion chromatography. Science 1995, 267, 1483.
23. (b) D. E. Clemmer, R. R. Hudgins, M. F. Jarrold. Naked protein conformations - cytochrome-c in the gas-phase. J. Am. Chem. Soc. 1995, 117, 10141.
24. (c) T.-Y. Kim, S. J. Valentine,D. E. Clemmer, J. P. Reilly. Gas-phase conformation-specific photofragmentation of proline-containing peptide ions. J. Am. Soc. Mass Spectrom. 2010, 21, 1455.
25. (a) K. Giles, S. D. Pringle, K. R. Worthington, D. Little, J. L. Wildgoose, R. H. Bateman. Applications of a travelling wave-based radio-frequencyonly stacked ring ion guide. Rapid Commun. Mass Spectrom. 2004, 18, 2401.
26. (b) S. D. Pringle, K. Giles, J. L. Wildgoose, J. P. Williams, S. E. Slade, K. Thalassinos, R. H. Bateman, M. T. Bowers, J. J. Scrivens. An investigation of the mobility separation of some peptide and protein ions using a new hybrid quadrupole/travelling wave IMS/oa-ToF instrument. Int. J. Mass Spectrom. 2007, 261, 1.
27. (c) A. A. Shvartsburg, R. D. Smith. Fundamentals of traveling wave ion mobility spectrometry. Anal. Chem. 2008, 80, 9689.
28. P. M. Lalli, B. A. Iglesias, D. K. Deda, H. E. Toma, G. F. Sa, R. J. Daroda, K. Araki, M. N. Eberlin. Resolution of isomeric multi-ruthenated porphyrins by travelling wave ion mobility mass spectrometry. Rapid Commun. Mass Spectrom. 2012, 26, 263.
29. (a) L. W. Beegle, I. Kanik, L. Matz, H. H. Hill. Effects of drift-gas polarizability on glycine peptides in ion mobility spectrometry. Int. J. Mass Spectrom. 2002, 216, 257.
30. (b) Z. Karpas, Z. Berant. Effect of drift gas on mobility of ions. J. Phys. Chem. 1989, 93, 3021.
31. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J.M.Millam, S. S. Iyengar, J. Tomasi, V. Barone, B.Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B.Cross,V. Bakken, C. Adamo, J. Jaramillo, R.Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K.Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople. Gaussian 03, Revision B.05. Gaussian, Inc.: Wallingford, CT, 2004.
32. (a) M. F. Mesleh, J. M. Hunter, A. A. Shvartsburg, G. C. Schatz, M. F. Jarrold. Structural information from ion mobility measurements: Effects of the long-range potential. J. Phys. Chem. 1996, 100, 16082.
33. (b) M. F. Jarrold. website. http://www.indiana.edu/~nano/software.html
34. G. J. Van Berkel, F. Zhou, J. T. Aronson. Changes in bulk solution pH caused by the inherent controlled-current electrolytic process of an electrospray ion source. Int. J. Mass Spectrom. 1997, 162, 55.
35. A. V. Robertson, M. Marx, C. Djerassi. Question of ring expansion in electron impact-induced fragmentation of aromatic amines. Chem. Commun. 1968, 206, 414.
36. Z. Karpas, M. J. Cohen, R. M. Stimac, R. F. Wernlund. On the effects of structure and charge-distribution on the mobility of ions. Int. J. Mass Spectrom.Ion Process. 1986, 74, 153.
37. (a) K. M. Kadish, K. M. Smith, R. Guilard. The Porphyrin Handbook, Vol. 1-20. Academic Press: San Diego, 2000-2003.
38. (b) J. Setsune. Palladium chemistry in recent porphyrin research. J. Porph. Phthalocyan. 2004, 8, 93.
39. R. C. Rocha, K. Araki, H. E. Toma. Intervalence transfer properties of the binuclear mu-benzotriazolate- and mu-benzimidazolate-bis {ruthenium(II)/(III)-edta} complexes. Inorg. Chim. Acta 1999, 285, 197.
40. (a) D. M. Tomazela, F. C. Gozzo, I. Mayer, F. M. Engelmann, K. Araki, H. E. Toma, M. N. Eberlin. Electrospray mass and tandem mass spectrometry of homologous and isomeric singly, doubly, triply and quadruply charged cationic ruthenated meso-(phenyl)(m)-(meta- and para-pyridyl)(n) (m + n = 4) macrocyclic porphyrin complexes. J. Mass Spectrom. 2004, 39, 1161.
41. (b) S. H. Toma, A. D. P. Alexiou, H. E. Toma, M. N. Eberlin, K. Araki. Can mass dissociation patterns of transition-metal complexes be predicted from electrochemical data? J. Mass Spectrom. 2009, 44, 361.
42. (a) H. Winnischofer, F. M. Engelmann, H. E. Toma, K. Araki. Acid-base and spectroscopic properties of a novel supramolecular porphyrin bonded to four pentacyanoferrate(II) groups. Inorg. Chim. Acta 2002, 338, 27.
43. (b) P. Stepanek, V. Andrushchenko, K. Ruud, P. Bour. Porphyrin protonation studied by magnetic circular dichroism. J. Phys. Chem. A 2012, 116, 778.
44. M. Eberlin. Structurally diagnostic ion/molecule reactions: class and functional-group identification by mass spectrometry. J. Mass Spectrom. 2006, 41, 141.