Silver cation affinities of monomeric building blocks of polyethers and polyphenols determined by guided ion beam tandem mass spectrometry

Journal of Physical Chemistry A

Volumn 117, Issue 34, 2013, Pages 8274-8284

  Chen, Y ^a   Chinthaka, S D M ^a   Rodgers, M T ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING CONFORMATIONS; BINDING GEOMETRIES; BOND DISSOCIATION ENERGIES; BUILDING BLOCKES; COLLISION-INDUCED DISSOCIATION; EFFECTIVE CORE POTENTIAL; GUIDED ION BEAM TANDEM MASS SPECTROMETRIES; NEUTRAL LIGANDS;

BINDING ENERGY; CHEMICAL BONDS; COMPLEXATION; ETHERS; ION BEAMS; LIGANDS; MASS SPECTROMETRY; METHANOL; PHENOLS; POLYETHERS; POSITIVE IONS;

SILVER;

EID: 84883338997     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp402224t     Document Type: Conference Paper

References (79)

1. Karas, M.; Bachmann, D.; Hillenkamp, F. Influence of the Wavelength in High Irradiance Ultraviolet Laser Desorption Mass Spectrometry of Organic Molecules Anal. Chem. 1985, 57, 2935-2939
2. Karas, M.; Bachmann, D.; Bahra, U.; Hillenkamp, F. Matrix-Assisted Ultraviolet Laser Desorption of Non-Volatile Compounds Int. J. Mass Spectrom. Ion Processes 1987, 78, 5368
3. Tanaka, K.; Wak, H.; Ido, Y.; Akita, S.; Yoshida, Y.; Yoshida, T. Protein and Polymer Analysis up to m/z 100,000 by Laser Ionization Time-of-Flight Mass Spectrometry Rapid Commun. Mass Spectrom. 1988, 2, 151-153
4. Karas, M.; Hillenkamp, F. Laser Desorption Ionization of Proteins with Molecular Masses Exceeding 10,000 Da Anal. Chem. 1988, 60, 2299-2301
5. Covey, T. R.; Huang, E. C.; Henion, J. D. Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry of Biopolymers Anal. Chem. 1991, 63, 1193A-1203A
6. Montaudo, G.; Samperi, F.; Montaudo, M. S. Characterization of Synthetic Polymers by MALDI-MS Prog. Polym. Sci. 2006, 31, 277-357
7. Blais, J.-C.; Turrin, C.-O.; Caminade, A.-M.; Majoral, J.-P. MALDI TOF Mass Spectrometry for the Characterization of Phosphorus-Containing Dendrimers. Scope and Limitations Anal. Chem. 2000, 72, 5097-5105
8. Chessa, G.; Scrivanti, A.; Seraglia, R.; Traldi, P. Matrix Effects on Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry Analysis of Dendrimers with a Pyridine-Based Skeleton Rapid Commun. Mass Spectrom. 1998, 12, 1533-1537
9. Puapaiboon, U.; Taylor, R. T. Characterization and Monitoring Reaction of Polyurethane Dendritic Wedges and Dendrimers Using Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry Rapid Commun. Mass Spectrom. 1999, 13, 508-515
10. Wetzel, S. J.; Guttman, C. M.; Flynn, K. M.; Filliben, J. J. Significant Parameters in the Optimization of MALDI-TOF-MS for Synthetic Polymers J. Am. Soc. Mass Spectrom. 2006, 17, 246-252
11. Mourey, T. H.; Hoteling, A. J.; Balke, S. T.; Owens, K. G. Molar Mass Distributions of Polymers from Size Exclusion Chromatography and Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry: Methods for Comparison J. Appl. Polym. Sci. 2005, 97, 627-639
12. Guttman, C. M.; Blair, W. R.; Danis, P. O. Mass Spectroscopy and SEC of SRM 1487, a Low Molecular Weight Poly(methyl methacrylate) Standard J. Polym. Sci., Part B: Polym. Phys. 1997, 35, 2409-2419
13. Zammit, M. D.; Davis, T. P.; Haddleton, D. M.; Suddaby, K. G. Evaluation of the Mode of Termination for a Thermally Initiated Free-Radical Polymerization via Matrix-Assisted Laser Desorption Ionization Time-of-Flight Mass Spectrometry Macromolecules 1997, 30, 1915-1920
14. Burton, R. D.; Watson, C. H.; Eyler, J. R.; Lang, G. L.; Powell, D. H.; Avery, M. Y. Proton Affinities of Eight Matrices Used for Matrix-Assisted Laser Desorption/Ionization Rapid Commun. Mass Spectrom. 1997, 11, 443-446
15. Steenvoorden, R. J. J. M.; Breuker, K.; Zenobi, R. The Gas Phase Basicity of MALDI Matrices Eur. Mass Spectrom. 1997, 3, 339-346
16. Breuker, K.; Knochenmuss, R.; Zenobi, R. Gas-Phase Basicities of Deprotonated Matrix-Assisted Laser Desorption/Ionization Matrix Molecules Int. J. Mass Spectrom. 1999, 184, 25-38
17. Yassin, F. H; Marynick, D. S. Computational Estimates of the Gas-Phase Basicities, Proton Affinities and Ionization Potentials of the Six Isomers of Dihydroxybenzoic Acid Mol. Phys. 2005, 103, 183-189
18. Chinthaka, S. D. M.; Chu, Y.; Rannulu, N. S.; Rodgers, M. T. Sodium Cation Affinities of MALDI Matrices Determined by Guided Ion Beam Tandem Mass Spectrometry: Application to Benzoic Acid Derivatives J. Phys. Chem. A 2006, 110, 1426-1437
19. Chinthaka, S. D. M.; Rodgers, M. T. Potassium Cation Affinities of Matrix Assisted Laser Desorption Ionization Matrices Determined by Threshold Collision-Induced Dissociation: Application to Benzoic Acid Derivatives J. Phys. Chem. A 2007, 111, 8152-8162
20. Chinthaka, S. D. M.; Rodgers, M. T. Sodium Cation Affinities of Commonly Used MALDI Matrices Determined by Guided Ion Beam Tandem Mass Spectrometry J. Am. Soc. Mass Spectrom. 2012, 23, 676-689
21. Nielen, M. W. F. MALDI Time-of-Flight Mass Spectrometry of Synthetic Polymers Mass Spectrom. Rev. 1999, 18, 309-344
22. Danis, P. O.; Karr, D. E. A Facile Sample Preparation For the Analysis of Synthetic Organic Polymers by Matrix-Assisted Laser Desorption/Ionization Org. Mass Spectrom. 1993, 28, 923-925
23. Erb, W. J.; Hanton, S. D.; Owens, K. G. A Study of Gas-Phase Cationization in Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry Rapid Commun. Mass Spectrom. 2006, 20, 2165-2169
24. Hanton, S. D.; Owens, K. G.; Chavez-Eng, C.; Hoberg, A. M.; Derrick, P. J. Updating Evidence for Cationization of Polymers in the Gas Phase during Matrix-Assisted Laser Desorption/Ionization Eur. J. Mass Spectrom. 2005, 11, 23-29
25. Mowat, I. A.; Donovan, R. J.; Maier, R. R. J. Enhanced Cationization of Polymers Using Delayed Ion Extraction with Matrix-Assisted Laser Desorption/Ionization Rapid Commun. Mass Spectrom. 1997, 11, 89-98
26. Llenes, C. F.; O'Malley, R. M.; Cotter, R. J. Cation Attachment in the Analysis of Polystyrene and Polyethylene Glycol by Laser-Desorption Time-of-Flight Mass Spectrometry Rapid Commun. Mass Spectrom. 1992, 6, 564-570
27. Mowat, I. A.; Donovan, R. J. Metal-Ion Attachment to Non-Polar Polymers During Laser Desorption/Ionization at 337 nm Rapid Commun. Mass Spectrom. 1995, 9, 82-90
28. Chaudhary, A. K.; Critchley, G.; Diaf, A.; Beckmann, E. J.; Russell, A. J. Characterization of Synthetic Polymers Using Matrix-Assisted Laser Desorption/Ionization-Time of Flight Mass Spectrometry Macromolecules 1996, 29, 2213-2221
29. Deery, M. J.; Jennings, K. R.; Jasieczek, C. B.; Haddleton, D. M.; Jackson, A. T.; Yates, H. T.; Scrivens, J. H. A Study of Cation Attachment to Polystyrene by Means of Matrix-Assisted Laser Desorption/Ionization and Electrospray Ionization-Mass Spectrometry Rapid Commun. Mass Spectrom. 1997, 11, 57-62
30. Zenobi, R.; Knochenmuss, R. Ion Formation in MALDI Mass Spectrometry Mass Spectrom. Rev. 1998, 17, 337-366
31. Knochenmuss, R. Ion Formation Mechanisms in UV-MALDI Analyst 2006, 131, 966-986
32. Hoberg, A. M.; Haddleton, D. M.; Derrick, P. J. Evidence for Cationization of Polymers in the Gas Phase During Matrix-Assisted Laser Desorption/Ionization Eur. J. Mass Spectrom. 1997, 3, 471-473
33. + Attachment to Polystyrene Rapid Commun. Mass Spectrom. 1998, 12, 801-804
34. Rashidezadeh, H.; Guo, B. Investigation of Metal Attachment to Polystyrenes in Matrix-Assisted Laser Desorption Ionization J. Am. Soc. Mass Spectrom. 1998, 9, 724-730
35. Wang, B. H.; Dreisewerd, K.; Bahr, U.; Karas, M.; Hillenkamp, F. Gas-Phase Cationization and Protonation of Neutrals Generated by Matrix-Assisted Laser Desorption J. Am. Soc. Mass Spectrom. 1993, 4, 393-398
36. Chen, W. Y.; Chen, Y. C. A Microwave-Assisted Click Chemistry Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via a Copper(I)-Catalyzed Three-Component Reaction Anal. Chem. 2003, 75, 4223-4225
37. Smirnov, I. P.; Zhu, H.; Taylor, T.; Huang, Y.; Ross, P.; Papayanopoulos, I. A.; Martin, S. A.; Pappin, D. J. Suppression of α-Cyano-4- hydroxycinnamic Acid Matrix Clusters and Reduction of Chemical Noise in MALDI-TOF Mass Spectrometry Anal. Chem. 2004, 76, 2958-2965
38. Rodgers, M. T. Substituent Effects in the Binding of Alkali Metal Ions to Pyridines, Studied by Threshold Collision-Induced Dissociation and Ab Initio Theory: The Methylpyridines J. Phys. Chem. A 2001, 105, 2374-2383
39. 2,HD) from Thermal to 30 eV c.m J. Chem. Phys. 1985, 83, 166-189
40. x (x = 1-4) for M = Ti to Cu Determined by Collision-Induced Dissociation J. Am. Chem. Soc. 1994, 116, 3519-3528
41. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Gaussian 98, revision A.11; Gaussian, Inc.: Pittsburgh, PA, 2001; (see the Supporting Information for full reference).
42. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
43. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula Into a Functional of the Electron Density Phys. Rev. B 1988, 37, 785-789
44. Bergner, A.; Dolg, M.; Kuechle, W.; Stoll, H.; Preuss, H. Ab-Initio Energy-Adjusted Pseudopotentials for Elements of Groups 13-17 Mol. Phys. 1993, 80, 1431-1441
45. Kaupp, M.; Schleyer, P. v. R.; Stoll, H.; Preuss, H. Pseudopotential Approaches to Ca, Sr, and Ba Hydrides. Why Are Some Alkaline Earth MX2 Compounds Bent? J. Chem. Phys. 1991, 94, 1360-1366
46. Dolg, M.; Stoll, H.; Preuss, H.; Pitzer, R. M. Relativistic and Correlation Effects for Element 105 (Hahnium, Ha): A Comparative Study of M and MO (M = Nb, Ta, Ha) Using Energy-Adjusted Ab Initio Pseudopotentials J. Phys. Chem. 1993, 97, 5852-5859
47. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Optimization of Gaussian-Type Basis Sets For Local Spin Density Functional Calculations. Part I. Boron Through Neon, Optimization Technique and Validation Can. J. Chem. 1992, 70, 560-571
48. Foresman, J. B.; Frisch, E. Exploring Chemistry with Electronic Structure Methods, 2 nd ed.; Gaussian: Pittsburgh, PA, 1996.
49. Boys, S. F.; Bernardi, R. Calculation of Small Molecular Interactions by Differences of Separate Total Energies-Some Procedures with Reduced Errors Mol. Phys. 1979, 19, 553-566
50. van Duijneveldt, F. B.; van Duijneveldt-van de Rijdt, J. G. C. M.; van Lenthe, J. H. State of the Art in Counterpoise Theory Chem. Rev. 1994, 94, 1873-1885
51. Muntean, F.; Armentrout, P. B. Guided Ion Beam Study of Collision-Induced Dissociation Dynamics: Integral and Differential Cross Sections J. Chem. Phys. 2001, 115, 1213-1228
52. Beyer, T. S.; Swinehart, D. F. Algorithm 448: Number of Multiply-Restricted Partitions Commun. ACM 1979, 16, 379
53. Stein, S. E.; Rabinovitch, B. S. Accurate Evaluation of Internal Energy Level Sums and Densities Including Anharmonic Oscillators and Hindered Rotors J. Chem. Phys. 1973, 58, 2438-2445
54. Stein, S. E.; Rabinovitch, B. S. On the Use of Exact State Counting Methods in RRKM Rate Calculations Chem. Phys. Lett. 1977, 49, 183-188
55. Pople, J. A.; Schlegel, H. B.; Raghavachari, K.; DeFrees, D. J.; Binkley, J. F.; Frisch, M. J.; Whitesides, R. F.; Hout, R. F.; Hehre, W. J. Molecular Orbital Studies of Vibrational Frequencies Int. J. Quantum Chem. Symp. 1981, 15, 269-278
56. DeFrees, D. J.; McLean, A. D. Molecular Orbital Predictions of the Vibrational Frequencies of Some Molecular Ions J. Chem. Phys. 1985, 82, 333-341
57. Rodgers, M. T.; Ervin, K. M.; Armentrout, P. B. Statistical Modeling of Collision-Induced Dissociation Thresholds J. Chem. Phys. 1997, 106, 4499-4508
58. +, x = 1-16 J. Phys. Chem. 1993, 97, 7978-7987
59. Chesnavich, W. J.; Bowers, M. T. Theory of Translationally Driven Reactions J. Phys. Chem. 1979, 83, 900-905
60. Yang, Z.; Rodgers, M. T. Theoretical Studies of the Unimolecular and Bimolecular Tautomerization of Cytosine Phys. Chem. Chem. Phys. 2004, 6, 2749-2757
61. Yang, Z.; Rodgers, M. T. Influence of Halogenation on the Properties of Uracil and Its Noncovalent Interactions with Alkali Metal Ions. Threshold Collision-Induced Dissociation and Theoretical Studies J. Am. Chem. Soc. 2004, 126, 16217-16226
62. x, x = 1-4. Competition Between Ion Solvation and Hydrogen Bonding Phys. Chem. Chem. Phys. 2005, 7, 1014-1025
63. Ruan, C.; Yang, Z.; Rodgers, M. T. Influence of the d Orbital Occupation on the Nature and Strength of Copper Cation-π Interactions: Threshold Collision-Induced Dissociation and Theoretical Studies Phys. Chem. Chem. Phys. 2007, 9, 5902-5918
64. Hallowita, N.; Carl, D. R.; Armentrout, P. B.; Rodgers, M. T. Dipole Effects on Cation-π Interactions: Absolute Bond Dissociation Energies of Complexes of Alkali Metal Cations to N -Methylaniline and N, N -Dimethylaniline J. Phys. Chem. A 2008, 112, 7996-8008
65. + with N-Donor Ligands (Pyridine, 4,4-Dipyridyl, 2,2-Dipyridyl, and 1,10-Phenanthroline): Collision-Induced Dissociation and Theoretical Studies J. Phys. Chem. A 2012, 116, 1319-1332
66. Chen, Y.; Rodgers, M. T. Structural and Energetic Effects in the Molecular Recognition of Protonated Peptidomimetic Bases by 18-Crown-6 J. Am. Chem. Soc. 2012, 134, 2313-2324
67. + with the Aromatic Amino Acids, Phenylalanine, Tyrosine, and Tryptophan J. Am. Chem. Soc. 2004, 126, 14600-14610
68. Armentrout, P. B.; Rodgers, M. T. An Absolute Sodium Cation Affinity Scale: Threshold Collision-Induced Dissociation Experiments and Ab Initio Theory J. Phys. Chem. A 2000, 104, 2238-2247
69. Rodgers, M. T.; Armentrout, P. B. Noncovalent Metal-Ligand Bond Energies as Studied by Threshold Collision-Induced Dissociation Mass Spectrom. Rev. 2000, 19, 215-247
70. Dalleska, N. F.; Honma, K.; Armentrout, P. B. Stepwise Solvation Enthalpies of Protonated Water Clusters: Collision-Induced Dissociation as an Alternative to Equilibrium Studies J. Am. Chem. Soc. 1993, 115, 12125-12131
71. Armentrout, P. B.; Simons, J. Understanding Heterolytic Bond Cleavage J. Am. Chem. Soc. 1992, 114, 8627-8633
72. Dunbar, R. C. Metal Cation Binding to Phenol: DFT Comparison of the Competing Sites J. Phys. Chem. A 2002, 106, 7328-7337
73. Amunugama, R.; Rodgers, M. T. The Influence of Substituents on Cation-π Interactons. 4. Absolute Binding Energies of Alkali Metal Cation-Phenol Complexes Determined by Threshold Collision-Induced Dissociation and Theoretical Studies J. Phys. Chem. A 2002, 106, 9718-9728
74. +-Phenol Ionic Complex J. Phys. Chem. A 2010, 114, 11053-11059
75. +(phenol) Complexes Using Infrared Spectroscopy J. Chem. Phys. 2004, 120, 721-730
76. + J. Am. Soc. Mass Spectrom. 2010, 21, 750-757
77. Shoeib, T.; Siu, K. W. M.; Hopkinson, A. C. Silver Ion Binding Energies of Amino Acids: Use of Theory to Assess the Validity of Experimental Silver Ion Basicities Obtained from the Kinetic Method J. Phys. Chem. A 2002, 106, 6121-6128
78. +, where n = 1-8: Competition Between Direct Coordination and Solvation Through Hydrogen Bonding Int. J. Mass Spectrom. 2000, 201, 87-100
79. Shoeib, T.; El Aribi, H.; Siu, K. W. M.; Hopkinson, A. C. A Study of Silver (I) Ion-Organonitrile Complexes: Ion Structures, Binding Energies, and Substituent Effects J. Phys.Chem. A 2001, 105, 710-719