Proton bound homodimers and heterodimers of amides and amines in the gas phase. Equilibrium studies by fourier transform ion cyclotron resonance spectrometry

Journal of the American Society for Mass Spectrometry

Volumn 13, Issue 11, 2002, Pages 1273-1281

  Witt, Matthias ^a   Grützmacher, Hans Friedrich ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CELLS; CHEMICAL BONDS; DISSOCIATION; FOURIER TRANSFORMS; MASS SPECTROMETRY; PROTONS;

HOMODIMERS;

DIMERS;

AMIDE; AMINE; BASE; DIMETHYL SULFOXIDE; LIGAND; N,N DIMETHYLFORMAMIDE; OLIGOMER; PROTON; AMMONIA;

AMIDE; AMINE; FOURIER TRANSFORM;

ALKALINITY; ARTICLE; BINDING AFFINITY; CALCULATION; CHEMICAL BOND; CHEMICAL REACTION; CORRELATION ANALYSIS; DISSOCIATION; ENERGY; FOURIER TRANSFORM ION CYCLOTRON RESONANCE SPECTROMETRY; GAS; MASS SPECTROMETRY; PROTON TRANSPORT; SOLVATION; ALGORITHM; CHEMISTRY; CYCLOTRON; FOURIER ANALYSIS; KINETICS;

ALGORITHMS; AMIDES; AMINES; AMMONIA; CYCLOTRONS; FOURIER ANALYSIS; GASES; KINETICS; LIGANDS; MASS SPECTROMETRY; PROTONS;

EID: 0036832563     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1044-0305(02)00457-9     Document Type: Article

References (42)

1. Franks F. Characterization of Proteins. 1988;Humana Press, Clifton.
2. (a) Fersht A.R. Enzyme Structure and Mechanism. 2nd ed. 1985;Freeman, New York
3. (b) Kirby A.J. Efficiency of Proton Transfer Catalysis in Models and Enzymes. Acc Chem Res. 30:1997;290-296.
4. (a) Green M.K., Lebrilla C.B. Ion-Molecule Reactions as Probes of Gas-Phase Structures of Peptides and Proteins. Mass Spectrom Rev. 16:1997;53-71
5. (b) Carr S.A., Hemling M.E., Bean M.F., Roberts G.R. Integration of Mass Spectrometry in Analytical Biotechnology. Anal Chem. 63:1991;2802-2824
6. (c) Fenselau C. MALDI-MS and Strategies for Protein Analysis. Anal Chem. 69:1997;661A-665A
7. (d) Jarrold M.F. Peptides and Proteins in the Gas Phase. Annu Rev Phys Chem. 51:2001;179-207.
8. 3. J Am Chem Soc. 117:1995;12840-12854
9. (b) Przybylski M., Glocker M.O. Elektrospray-Massenspektrometrie von Biomolekülkomplexen mit nichtkovalenten Wechselwirkungen - neue analytische Perspektiven für supramolekulare Chemie und molekulare Erkennungsprozesse. Angew Chem. 108:1996;878-899. ; and Angew. Chem. Int. Ed. Engl. 1966, 35, 806-826.
10. (b) Przybylski M., Glocker M.O. Elektrospray-Massenspektrometrie von Biomolekülkomplexen mit nichtkovalenten Wechselwirkungen - neue analytische Perspektiven für supramolekulare Chemie und molekulare Erkennungsprozesse. Angew Chem. 108:1996;878-899. ; and Angew. Chem. Int. Ed. Engl. 1966, 35, 806-826.
11. (c) Wyttenbach T., Bowers M.T. Gas Phase Conformations of Biological Molecules The Hydrogen/Deuterium Exchange Mechanism . J Am Soc Mass Spectrom. 10:1999;9-14
12. (d) Jarrold M.F. Unfolding, Refolding, and Hydration of Proteins in the Gas Phase. Acc Chem Res. 32:1999;360-367
13. (e) McLafferty F.W., Cuan Z., Haupts U., Wood T.D., Kelleher N.L. Gaseous Conformational Structures of Cyctochrome c. J Am Soc Chem. 120:1998;4732-4740.
14. (a) Meot-Ner (Mautner) M. The Ionic Hydrogen Bond. IV. Intramolecular and Multiple Bonds. Protonation and Complexes of Amides and Amino Acids Derivatives. J Am Chem Soc. 106:1984;278-283
15. (b) Meot-Ner (Mautner) M. Models for Strong Interaction in Proteins and Enzymes. II. Interactions of Ions with the Peptide Link and with Imidazole. J Am Chem Soc. 110:1988;3075-3080.
16. (a) Witt M., Grützmacher H.-F. The Gas Phase Basicity and Proton Affinity of Propionamide. A Comparison of Methods. Int J Mass Spectrom. 164:1997;93-106
17. (b) Witt M., Grützmacher H.-F. Proton-Bound Dimers of Aliphatic Carboxamides Gas-Phase Basicity and Dissociation Energy . Int J Mass Spectrom. 165/166:1997;49-62.
18. Witt M., Grützmacher H.-F. Effects of Internal Hydrogen Bonds Between Carboxamide Groups Gas-Phase Basicity and Proton Affinity of Linear Aliphatic Diamides . Eur Mass Spectrom. 6:2000;97-107.
19. (a) Cooks R.G., Kruger T.L. Intrinsic Basicity Determination Using Metastable Ions. J Am Chem Soc. 99:1977;1279-1281
20. (b) Cooks R.G., Pattrick J.S., Kotiaho T., McLuckey S.A. Thermochemical Determinations by the Kinetic Method. Mass Spectrom Rev. 13:1994;287-339
21. (c) Cooks R.G., Koskinen J.T., Thomas P.D. The Kinetic Method of Making Thermochemical Determinations. J Mass Spectrom. 34:1999;85-92.
22. + Complexes (E = P, As, Sb, Bi) . Int J Mass Spectrom Ion Processes. 157/158:1996;233-247.
23. Rodgers M.T., Armentrout P.B. Noncovalent Metal-Ligand Bond Energies as Studied by Threshold Collision-Induced Dissociation. Mass Spectrom Rev. 19:2001;215-247.
24. (a) Larson J.W., McMahon T.B. Formation, Thermochemistry and Relative Stabilities of Proton-Bound Dimers of Oxygen n-Donor Bases from Ion Cyclotron Resonance Solvent-Exchange Equilibria Measurements. J Am Chem Soc. 104:1982;6255-6261
25. (b) Cao J., Holmes J.L. The Determination of Proton Affinities of Secondary Alcohols from the Dissociation of Proton Bound Molecular Trios. Eur J Mass Spectrom. 7:2001;243-246.
26. Witt, M. Dissertation, (Gasphasenreaktionen protonengebundener Amidcluster); Universität Bielefeld, 1998.
27. Witt, M.; Grützmacher, H.-F. Ligand Exchange Reactions of Proton Bound Dimers of Carboxamides - Models for Protonated Proteins. Int. J. Mass Spectrom., in press.
28. (a) Allemann M., Kellerhals H.P., Wanczek K.P. High Magnetic Field Fourier Transform Ion Cyclotron Resonance Spectroscopy. Int J Mass Spectrom Ion Processes. 46:1983;139-142
29. (b) Kofel P., Allemann M., Kellerhals H.P., Wanczek K.P. External Generation of Ions in ICR Spectrometry. Int J Mass Spectrom Ion Processes. 65:1985;97-103.
30. Caravatti P., Alleman M. The "Infinity Cell:" A New Trapped-Ion Cell With Radio-Frequency Covered Trapping Electrodes for Fourier Transform Ion Cyclotron Resonance Mass Spectrometry . Org Mass Spectrom. 26:1991;514-518.
31. Microcal Origin 4.1, Microcal Software Inc.: Northampton, MA, 1996.
32. Anicich V.G. Evaluated Bimolecular Ion-Molecule Gas Phase Kinetics of Positive Ions for Use in Modeling Planetary Atmosphere, Cometary Comae, and Interstellar Clouds. J Phys Chem Ref Data. 22:1993;1469-1569.
33. Bartmess J.E., Georgiadis R.M. Empirical Methods for Determination of Ionization Gauge Relative Sensitivities for Different Gases. Vacuum. 33:1983;149-153.
34. Witt, M.; Grützmacher, H.-F. to be published.
35. All GB and PA were taken from NIST Standard Reference Database No. 69 - Release February 2000 (http//webbook.nist.gov./chemistry).
36. (a) Davidson W.R., Sunner J., Kebarle P. Hydrogen Bonding of Water to Onium ions. Hydration of Substituted Pyridinium Ions and related Systems. J Am Chem Soc. 101:1979;1675
37. (b) Meot-Ner (Mautner) M. The Ionic Hydrogen Bond. II. Protonation and Complexes of Amines, Alcohol, and Ethers. J Am Chem Soc. 106:1984;1257
38. (c) Speller C.V., Meot-Ner (Mautner) M. The Ionic Hydrogen Bond and Ion Solvation. III. Bonds Involving Cyanides. Correlations with Proton Affinities. J Phys Chem. 89:1985;5217.
39. (a) Scheiner S., Wang L. Hydrogen Bonding and Proton Transfers of the Amide Group. J Am Chem Soc. 115:1993;1958-1963
40. (b) Scheiner S. Bent Hydrogen Bonds and Proton Transfers. Acc Chem Res. 27:1994;402-408
41. (c) Perrin C.L. Proton Exchange in Amides Surprises from Simple Systems . Acc Chem Res. 22:1989;268-275
42. (d) Perrin C.L., Nielson J.B. "Strong" Hydrogen Bonds in Chemistry and Biology. Ann Rev Phys Chem. 48:1997;511-544.