Reactions of organic ions at ambient surfaces in a solvent-free environment

Journal of the American Society for Mass Spectrometry

Volumn 23, Issue 5, 2012, Pages 842-849

  Badu Tawiah, Abraham K ^a   Cyriac, Jobin ^a   Cooks, R Graham ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

Atmospheric pressure mass spectrometry; Ion soft landing; Ion surface reactions; Solvent free reactions; Surface enhanced raman spectroscopy

Indexed keywords

DRYING TUBES; ELECTROSPRAYING; ETHANOLAMINES; EX SITU; GOLD SUBSTRATES; H/D EXCHANGE; IN-SITU; ISOMERIC PRODUCTS; MINOR PRODUCTS; NUCLEOPHILIC GROUPS; ORGANIC AMINE; ORGANIC IONS; ORGANIC SALT; POLYATOMIC ION; PYRIDINIUM; PYRYLIUM; REGIOSPECIFIC; SOFT LANDING; SOLID-PHASE; SOLVENT FREE; SOLVENT FREE REACTION; SURFACE ENHANCED RAMAN SPECTROSCOPY;

ATMOSPHERIC PRESSURE; ELECTRIC FIELDS; GOLD COATINGS; LIGHT TRANSMISSION; MASS SPECTROMETRY; ORGANIC COMPOUNDS; RAMAN SPECTROSCOPY; REACTION PRODUCTS; SOLVENTS; SURFACE REACTIONS;

POSITIVE IONS;

2,4,6 TRIPHENYLPYRYLIUM; AMINE; ANION; ETHANOLAMINE; GOLD; NUCLEOPHILE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC PRESSURE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEUTERIUM HYDROGEN EXCHANGE; ELECTRIC FIELD; ELECTROSPRAY; ELECTROSPRAY MASS SPECTROMETRY; MASS SPECTROMETRY; RAMAN SPECTROMETRY; SURFACE PROPERTY;

EID: 84862536151     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-012-0337-7     Document Type: Article

References (44)

1. Rogers, J.A., Someya, T., Huang, Y.: Materials and Mechanics for Stretchable Electronics. Science 327, 1603-1606 (2010)
2. Currie, M.J., Mapel, J.K., Heidel, T.D., Goffri, S., Baldo, M.A.: Highefficiency Organic Solar Concentrators for Photovoltaics. Science 321, 226-228 (2008) (Pubitemid 351989089)
3. Forrest, S.R., Thompson, M.E.: Introduction: Organic Electronics and Optoelectronics. Chem Rev 107, 923-925 (2007) (Pubitemid 46736531)
4. Johnson, G.E., Laskin, J.: Preparation of Surface Organometallic Catalysts by Gas-Phase Ligand Stripping and Reactive Landing of Mass-Selected Ions. Chem Eur J 16, 14433-14438 (2010)
5. Davila, S.J., Birdwell, D.O., Verbeck, G.F.: Drift Tube Soft-Landing for the Production and Characterization of Materials: Applied to Cu Clusters. Rev Sci Instrum 81, 034104 (2010)
6. Mmereki, B.T., Donaldson, D.J., Gilman, J.B., Eliason, T.L., Vaida, V.: Kinetics and Products of the Reaction of Gas-Phase Ozone with Anthracene adsorbed at the air-aqueous interface. Atmos Env 38, 6091-6013 (2004)
7. Mmereki, B.T., Donaldson, D.J.: Direct Observation of the Kinetics of an Atmospherically Important Reaction at the Air-aqueous Interface. J Phys Chem A 107, 11038-11042 (2003)
8. Sadiki, M., Quentel, F., Elleouet, C., Stephan, L., Olier, R., Privat, M.: Coadsorption at the Air/Water Interface as a Source of Pollutant Transfer to the Atmosphere: The Case Study of Benzene/Cyclohexane Traces and Lead. Atmos Env 39, 2661-2672 (2005)
9. 2SO4 Aerosol with Ammonia. J Aerosol Sci 23, 315-325 (1992)
10. Thornton, J.A., Abbatt, J.P.D.: N2O5 Reaction on Submicron Sea Salt Aerosol: Kinetics, Products, and the Effect of Surface Active Organics. J Phys Chem A 109, 10004-10012 (2005) (Pubitemid 41698277)
11. Lawrence, J.R., Glass, S.V., Park, S.C., Nathanson, G.M.: Evaporation of Water through Butanol Films at the Surface of Supercooled Sulfuric Acid. J Phys Chem A 109, 7458-7465 (2005)
12. Katrib, Y., Martin, S.T., Hung, H.M., Rudich, Y., Zhang, H.Z., Slowik, J.G., Davidovits, P., Jayne, J.T., Worsnop, D.R.: Products and Mechanisms of Ozone Reactions with Oleic Acid for Aerosol ParticlesHaving Core-Shell Morphologies. J Phys Chem A 108, 6686-6695 (2004)
13. Knopf, D.A., Anthony, L.M., Bertram, A.K.: Reactive Uptake of O3 by Multicomponent and Multiphase Mixtures Containing Oleic Acid J. Phys Chem A 109, 5579-5589 (2005) (Pubitemid 41027878)
14. Kalberer, M., Paulsen, D., Sax, M., Steinbacher, M., Dommen, J., Prevot, A.S.H., Fisseha, R., Weingartner, E., Frankevich, V., Zenobi, R., Baltensperger, U.: Identification of Polymers as Major Components of Atmospheric Organic Aerosols. Science 303, 1659-1662 (2004) (Pubitemid 38338322)
15. Strekowski, R.S., Remorov, R., George, C.: Direct Kinetic Study of the Reaction of Cl2 -Radical Anions with Ethanol at the Air-Water interface. J Phys Chem A 107, 2497-2504 (2003)
16. Kuznetsova, M., Lee, C.: Enhanced Extracellular Enzymatic Peptide Hydrolysis in the Sea Surface Microlayer. Mar Chem 73, 319-332 (2001) (Pubitemid 32139775)
17. Fenn, B., Mann, M., Meng, C.K., Wong, S.F., Whitehouse, C.M.: Electrospray ionization for mass spectrometry of large biomolecules. Science 246, 64-71 (1989) (Pubitemid 19252085)
18. Marquez, A.; Fabbretti, F.; Metzger, J. O. Electrospray Ionization Mass Spectrometric Study on the Direct Organocatalytic a-Halogenation of Aldehydes. Angew. Chem. 119, 7040-7042; Angew. Chem. Int. Ed. 2007, 46, 6915-6917 (2007)
19. Santos, L. S.; Metzger, J. O. Study of Homogeneously Catalyzed Ziegler-Natta Polymerization of Ethene Using Electrospray Ionization Mass Spectrometry. Angew. Chem. 118, 991-995; Angew. Chem. Int. Ed. 2006, 45, 977-981 (2006)
20. Eberlin, M.N.: Electrospray Ionization Mass Spectrometry: A Major Tool to Investigate Reaction Mechanism in both Solution and Gas-Phase. Eur J Mass Spectrom 13, 19 (2007)
21. Hamill, W.H.: Ion-Molecule Reactions. J Chem Educ 36(7), 346-349 (1959)
22. Volny, M., Elam, W.T., Branca, A., Ratner, B.D., Turecek, F.: Preparative Soft and Reactive Landing of Multiply Charged Protein Ions on a Plasma-Treated Metal Surface. Anal Chem 77, 4890-4896 (2005) (Pubitemid 41076680)
23. Hu, Q., Wang, P., Gassman, P.L., Laskin, J.: In situ Studies of Soft-and Reactive Landing of Mass-Selected Ions Using Infrared Reflection Absorption Spectroscopy. Anal Chem 81, 7302-7308 (2009)
24. Franchetti, V., Solka, B.H., Baitinger, W.E., Amy, J.W., Cooks, R.G.: Soft Landing of Ions as a Means of Surface Modification. Int J Mass Spectrom Ion Phys 23(1), 29-35 (1977)
25. Siuzdak, G., Hollenbeck, T., Bothner, B.: Preparative Mass Spectrometry with Electrospray Ionization. J Mass Spectrom 34, 1087 (1999)
26. Rauschenbach, S., Stadler, F.L., Lunedei, E., Malinowski, N., Koltsov, S., Costantini, G., Kern, K.: Electrospray Ion Beam Depos Clust Biomol Small 2(4), 540-547 (2006)
27. Chen, H., Eberlin, L.S., Cooks, R.G.: Neutral Fragment Mass Spectra after Ambient Thermal Dissociation of Peptide and Protein Ions. J Am Chem Soc 129(18), 5880-5886 (2007) (Pubitemid 46748492)
28. Eberlin, L.S., Xia, Y., Chen, H., Cooks, R.G.: Atmospheric Pressure Thermal Dissociation of Phospho-and Sulfopeptides. J Am Soc Mass Spectrom 19, 1897-1905 (2008)
29. Badu-Tawiah, A., Wu, C., Cooks, R.G.: Ambient Ion Soft Landing. Anal Chem 83, 2648-2654 (2011)
30. Chen, H., Eberlin, L.S., Neflui, M., Augusti, R., Cooks, R.G.: Organic Reactions of Ionic Intermediates Promoted by Atmospheric-Pressure Thermal Activation. Angew Chem Int Ed 47, 3422-4325 (2008)
31. Chen, H.; Ouyang, Z. Cooks, R. G. Thermal Production and Reactions of Organic Ions at Atmospheric Pressure. Angew. Chem. Int. Ed. 45, 3656-366 (2006)
32. Bose, A. K.; Manhas, M. S.; Ganguly, S. N.; Sharma, A. H.; Banik, B. K. More Chemistry for Less Pollution: Applications for Process Development. Synthesis. 1578 (2002)
33. Nuchter, M., Ondruschka, B., Bonrath, W., Gum, A.: Microwave Assisted Synthesis-A Critical tTchnology Overview. Green Chem 6, 128-141 (2004) (Pubitemid 38406301)
34. Balema, V.P., Wiench, J.W., Pruski, M., Pecharsky, V.K.: Mechanically Induced Solid-State Generation of Phosphorus Ylides and the Solvent-Free Wittig Reaction. J Am Chem Soc 124, 6244-6245 (2002) (Pubitemid 34579370)
35. Leung, S.H., Angel, S.A.: Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment. J Chem Educ 81(10), 1492-1493 (2004)
36. Katritzky, A.R., Marson, C.M.: Pyrylium Mediated Transformations of Primary Amino Groups into Other Functional Groups. Angew Chem Int Ed Engl 23, 420-429 (1984)
37. Katritzky, A. R.; Mokrosz, J. L.; De Rose, M. J. Pyrylium-mediated Transformations of Natural Products. Part 2. Reaction of 4-(4-methoxy-3- sulphophenyl)-2,6-bis-(4-sulphophenyl)pyrylium Perchlorate with Primary Amines. Chem. Soc. Perkin Trans. II. 5, 849-855 (1984)
38. Lekeufack, D.D., Brioude, A., Mouti, A., Alauzun, J.G., Stadelmann, P., Coleman, A.W., Mielea, P.: Core-shell Au(TiO2, SiO2) Nanoparticles with Tunable Morphology. Chem Commun 46, 4544-4546 (2010)
39. Jang, N.H.: SERS Analysis of CMC on Gold-Assembled Micelle. Bull Korean Chem Soc 25(9), 1392-1396 (2004)
40. Chang, H., Hwang, K.-C.: The Behavior of Pyridine, Pyridinium Ion, and Pyridinium Halide on a Silver Electrode and their SERS Spectra. J Am Chem Soc 106, 6586-6592 (1984) (Pubitemid 14667390)
41. Herne, T.M., Garrell, R.L.: Borate Interference in Surface-Enhanced Raman Spectroscopy of Amines. Anal Chem 63, 2290-2294 (1991)
42. Bozzinia, B., Mele, C., Tadjeddine, A.: Electrochemical Adsorption of Cyanide on Ag(1 1 1) in the Presence of Cetylpyridinium Chloride. J Crystal Growth 271, 274-286 (2004)
43. Choi, C.H., Kertesz, M.: Conformational Studies of Vibrational Properties and Electronic States of Leucoemeraldine Base and Its Oligomers. Macromolecules 30, 620-630 (1997) (Pubitemid 127567654)
44. Katritzky, A.R.: Conversions of Primary Amino Groups into other Functionality Mediated by Pyrylium Cations. Tetrahedron 36, 679-699 (1979)