N-centered odd-electron ions formation from collision-induced dissociation of electrospray ionization generated even-electron ions: Single electron transfer via ion/neutral complex in the fragmentation of protonated N,N′-dibenzylpiperazines and protonated N-benzylpiperazines

Journal of the American Society for Mass Spectrometry

Volumn 22, Issue 9, 2011, Pages 1526-1533

  Chai, Yunfeng ^a   Sun, Hezhi ^a   Pan, Yuanjiang ^a   Sun, Cuirong ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Electrospray Ionization Mass Spectrometry; Even Electron Ion; Ion Neutral Complex; N Benzylpiperazine; Odd Electron Ion; Single Electron Transfer

Indexed keywords

ELECTROSPRAY IONIZATION MASS SPECTROMETRY; EVEN-ELECTRON ION; N-BENZYLPIPERAZINE; ODD-ELECTRON ION; SINGLE ELECTRON TRANSFER;

DENSITY FUNCTIONAL THEORY; DISSOCIATION; ELECTRON TRANSITIONS; ELECTROSPRAY IONIZATION; FREE RADICAL REACTIONS; IONIZATION; IONS; MASS SPECTROMETRY; PROTONATION; SINGLE ELECTRON TRANSISTORS; TRANSIENTS;

ELECTRON AFFINITY;

CATION; EVEN ELECTRON ION; ION; N BENZYLPIPERAZINE; N,N' DIBENZYLPIPERAZINE; ODD ELECTRON ION; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLLISIONALLY ACTIVATED DISSOCIATION; COMPLEX FORMATION; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; DISSOCIATION; ELECTRON; ELECTRON TRANSPORT; ELECTROSPRAY; ELECTROSPRAY MASS SPECTROMETRY; ENERGY; ION NEUTRAL COMPLEX; PROTON TRANSPORT; SINGLE ELECTRON TRANSFER;

EID: 80052669931     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-011-0176-y     Document Type: Article

References (42)

1. M Karni A Mandelbaum 1980 The Even-Electron Rule Org. Mass Spectrom. 15 53 64 10.1002/oms.1210150202 1:CAS:528:DyaL3cXltFegt7Y%3D
2. RD Bowen AG Harrison 1981 Loss of Methyl Radical from Some Small Immonium Ions: Unusual Violation of the Even-Electron Rule Org. Mass Spectrom. 16 180 182 10.1002/oms.1210160408 1:CAS:528:DyaL3MXksl2ntLY%3D
3. M Ohashi RP Barron WR Benson 1981 Electron Impact-Induced Fragmentation of Quaternary Ammonium Cations J. Am. Chem. Soc. 103 3943 3945 10.1021/ja00403a064 1:CAS:528:DyaL3MXktlCis7s%3D
4. L Ceraulo P Agozzino M Ferrugia L Lamartina MC Natoli 1991 Studies in Organic Mass Spectrometry, Part 9-Mass Spectra of 9,10-Disubstituted 2,3,6,7-Tetraalkoxy-9,10-Dihydroanthracenes: A Remarkable Loss of Radicals from Even-Electron Ions Org. Mass Spectrom. 26 279 286 10.1002/oms.1210260419 1:CAS:528:DyaK3MXksVylt7g%3D
5. 3OH Adduct of Michler's Hydrol Blue: Proton-Shuttle Catalysis and Stepwise Radical Expulsions J. Phys. Chem. A 11 8925 8933 10.1021/jp073950g (Pubitemid 47522542)
6. EM Thurman I Ferrer OJ Pozo JV Sancho F Hernandez 2007 The Even-Electron Rule in Electrospray Mass Spectra of Pesticides Rapid Commun. Mass Spectrom. 21 3855 3868 10.1002/rcm.3271 1:CAS:528:DC%2BD2sXhsVWitL3L (Pubitemid 350220694)
7. JP Williams NMM Nibbering BN Green VJ Patel JH Scrivens 2006 Collision-Induced Fragmentation Pathways Including Odd-Electron Ion Formation from Desorption Electrospray Ionization Generated Protonated and Deprotonated Drugs Derived from Tandem Accurate Mass Spectrometry J. Mass Spectrom. 41 1277 1286 10.1002/jms.1091 1:CAS:528:DC%2BD28XhtFynurfP (Pubitemid 44671879)
8. K Levsen H-M Schiebel JK Terlouw KJ Jobst M Elend A Preiβ H Thiele A Ingendoh 2007 Even-Electron Ions: A Systematic Study of the Neutral Species Lost in the Dissociation of Quasimolecular Ions J. Mass Spectrom. 42 1024 1044 10.1002/jms.1234 1:CAS:528:DC%2BD2sXpsVGmsbg%3D (Pubitemid 47255454)
9. K Chen NS Rannulu Y Cai P Lane AL Liebl BB Rees C Corre GL Challis RB Cole 2008 Unusual Odd-Electron Fragments from Even-Electron Protonated Prodiginine Precursors Using Positive-Ion Electrospray Tandem Mass Spectrometry J. Am. Soc. Mass Spectrom. 19 1856 1866 10.1016/j.jasms.2008.08.002 1:CAS:528:DC%2BD1cXhsVyrtrnJ
10. R Vessecchi CA Carollo JNC Lopes AEM Crotti NP Lopes SE Galembeck 2009 Gas-Phase Dissociation of 1,4-Naphthoquinone Derivative Anions by Electrospray Ionization Tandem Mass Spectrometry J. Mass Spectrom. 44 1224 1233 10.1002/jms.1600 1:CAS:528:DC%2BD1MXhtVCgu7nE
11. Y Cai Z Mo NS Rannulu B Guan S Kannupal BC Gibb RB Cole 2010 Characterization of an Exception to the 'Even-Electron Rule' Upon Low-Energy Collision Induced Decomposition in Negative Ion Electrospray Tandem Mass Spectrometry J. Mass Spectrom. 45 235 240 10.1002/jms.1706 1:CAS:528: DC%2BC3cXjtFSjtLc%3D
12. G Xu T Huang J Zhang JK Huang T Carlson S Miao 2010 Investigation of Collision-Induced Dissociations Involving Odd-Electron Ion Formation Under Positive Electrospray Ionization Conditions Using Accurate Mass Rapid Commun. Mass Spectrom. 24 321 327 10.1002/rcm.4393 1:CAS:528:DC%2BC3cXlvVWhtQ%3D%3D
13. N Hu Y-P Tu K Jiang Y Pan 2010 Intramolecular Charge Transfer in the Gas Phase: Fragmentation of Protonated Sulfonamides in Mass Spectrometry J. Org. Chem. 75 4244 4250 10.1021/jo100761k 1:CAS:528:DC%2BC3cXmt1agtL8%3D
14. DJ McAdoo 1988 Ion-Neutral Complexes in Unimolecular Decompositions Mass Spectrom. Rev. 7 363 393 10.1002/mas.1280070402 1:CAS:528:DyaL1MXhtFeqsrg%3D
15. RD Bowen 1991 Ion-Neutral Complexes Acc. Chem. Res. 24 364 371 10.1021/ar00012a002 1:CAS:528:DyaK3MXmsl2jtrY%3D
16. TH Morton 1992 The Reorientation Criterion and Positive Ion-Neutral Complexes Org. Mass Spectrom. 27 353 368 10.1002/oms.1210270404 1:CAS:528:DyaK38Xkt1Gls7Y%3D
17. P Longevialle 1992 Ion-Neutral Complexes in the Unimolecular Reactivity of Organic Cations in the Gas Phase Mass Spectrom. Rev. 11 157 192 10.1002/mas.1280110302 1:CAS:528:DyaK38XmtFWlu7k%3D
18. M Edelson-Averbukh A Mandelbaum 2003 Intramolecular Electrophilic Aromatic Substitution in Gas-Phase-Protonated Difunctional Compounds Containing One or Two Arylmethyl Groups J. Mass Spectrom. 38 1169 1177 10.1002/jms.537 1:CAS:528:DC%2BD3sXpslGkurw%3D (Pubitemid 37508684)
19. J Bialecki J Ruzicka AB Attygalle 2006 An Unprecedented Rearrangement in Collision-Induced Mass Spectrometric Fragmentation of Protonated Benzylamines J. Mass Spectrom. 41 1195 1204 10.1002/jms.1089 1:CAS:528:DC%2BD28XhtVCks7zF (Pubitemid 44454173)
20. Y Chen C Le Droumaguet K Li WE Cotham N Lee M Walla Q Wang 2010 A Novel Rearrangement of Fluorescent Human Thymidylate Synthase Inhibitor Analogues in ESI Tandem Mass Spectrometry J. Am. Soc. Mass Spectrom. 21 403 410 10.1016/j.jasms.2009.11.004 1:CAS:528:DC%2BC3cXitlSnuro%3D
21. Y Chai K Jiang Y Pan 2010 Hydride Transfer Reactions Via Ion-Neutral Complex: Fragmentation of Protonated N-benzylpiperidines and Protonated N-Benzylpiperazines in Mass Spectrometry J. Mass Spectrom. 45 496 503 10.1002/jms.1731 1:CAS:528:DC%2BC3cXls1yqtr0%3D
22. Kuck, D., Grützmacher, H.-F., Barth, D., Heitkamp, S., Letzel, M.C.: The Role of Ion/Neutral Complexes in the Fragmentation of N-Benzyl- (Alkylpyridinium) Ions. Int. J. Mass Spectrom. (2011). doi: 10.1016/j.ijms.2010. 10.006
23. Y-P Tu Y Huang C Atsriku Y You J Cunniff 2009 Intramolecular Transacylation: Fragmentation of Protonated Molecules via Ion-Neutral Complexes in Mass Spectrometry Rapid Commun. Mass Spectrom. 23 1970 1976 10.1002/rcm.4108 1:CAS:528:DC%2BD1MXntFaqt7o%3D
24. P Liu N Hu Y Pan Y Tu 2010 Ion-Neutral Complexes Resulting from Dissociative Protonation: Fragmentation of α-Furanylmethyl Benzyl Ethers and 4-N, N-Dimethylbenzyl Benzyl Ethers J. Am. Soc. Mass Spectrom. 21 626 634 10.1016/j.jasms.2009.12.005 1:CAS:528:DC%2BC3cXjvFyntbg%3D
25. J Liu R Zhang J He Y Liu J Shi Z Abliz 2010 The Characteristic Fragmentation and Rearrangement Reaction of Cationized Glucopyranosyloxybenzyl Tartrates by Tandem Mass Spectrometry J. Mass Spectrom. 45 824 828 10.1002/jms.1770 1:CAS:528:DC%2BC3cXovVCgsL0%3D
26. A Pross 1985 The Single Electron Shift as a Fundamental Process in Organic Chemistry: The Relationship Between Polar and Electron-Transfer Pathways J. Am. Chem. Soc. 18 212 219 1:CAS:528:DyaL2MXlsVWjt78%3D
27. A Houmam 2008 Electron Transfer Initiated Reactions: Bond Formation and Bond Dissociation Chem. Rev. 108 2180 2237 10.1021/cr068070x 1:CAS:528:DC%2BD1cXotlOmtr4%3D
28. C-C Han JI Brauman 1988 Electron Transfer Competes with Proton Transfer in Gas-Phase Acid-Base Reactions J. Am. Chem. Soc. 110 4048 4049 10.1021/ja00220a059 1:CAS:528:DyaL1cXktVKjsb0%3D
29. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery Jr., J.A., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., Pople, J.A.: Gaussian 03, Revision B. Gaussian, Inc., Pittsburgh, PA (2003)
30. + Ratios After Charge Transfer to Ethylbenzene J. Phys. Chem. A 108 5600 5609 10.1021/jp031328s 1:CAS:528:DC%2BD2cXksVKht7w%3D
31. C-H Shin S-J Kim 2005 Theoretical Study for the Molecular Structures and Spectroscopic Properties of Various C7H7+ Isomers and Transition States Between them J. Korean Chem. Soc. 49 247 254 10.5012/jkcs.2005.49.3.247 1:CAS:528:DC%2BD2MXnvVagsbY%3D (Pubitemid 41050749)
32. E-L Zins C Pepe D Schröder 2010 Energy-Dependent Dissociation of Benzylpyridinium Ions in an Ion-Trap Mass Spectrometer J. Mass Spectrom. 45 1253 1260 10.1002/jms.1847 1:CAS:528:DC%2BC3cXhsV2ku73I
33. KV Barylyuk K Chingin RM Balabin R Zenobi 2010 Fragmentation of Benzylpyridinium "Thermometer" Ions and Its Effect on the Accuracy of Internal Energy Calibration J. Am. Soc. Mass Spectrom. 21 172 177 10.1016/j.jasms.2009.09.023 1:CAS:528:DC%2BC3cXjslykuw%3D%3D
34. E-L Zins C Pepe D Rondeau S Rochut N Galland J-C Tabet 2009 Theoretical and Experimental Study of Tropylium Formation from Substituted Benzylpyridinium Species J. Mass Spectrom. 44 12 17 10.1002/jms.1461 1:CAS:528: DC%2BD1MXhs1KktL8%3D
35. E-L Zins D Rondeau P Karoyan C Fosse S Rochut C Pepe 2009 Investigations of the Fragmentation Pathways of Benzylpyridinium Ions Under ESI/MS Conditions J. Mass Spectrom. 44 1668 1675 1:CAS:528:DC%2BD1MXhsF2jur7M
36. E-L Zins C Pepe D Schröder 2010 Methylene-Transfer Reactions of Benzylium/Tropylium Ions with Neutral Toluene Studied by Means of Ion-Trap Mass Spectrometry Faraday Discuss. 145 157 169 10.1039/b907236e 1:CAS:528: DC%2BC3cXntlKgtg%3D%3D
37. PA Karr ME Zandler M Beck JD Jaeger AL McCarty PM Smith F D'Souza 2006 Predicting the Site of Electron Transfer Using DFT Frontier Orbitals: Studies on Porphyrin Attached Either to Quinone or Hydroquinone, and Quinhydrone Self-Assembled Supramolecular Complexes THEOCHEM 765 91 103 10.1016/j.theochem. 2006.03.012 1:CAS:528:DC%2BD28XlvFGgs7Y%3D
38. A Chakraborty S Kar N Guchhait 2006 Secondary Amino Group as Charge Donor for the Excited State Intramolecular Charge Transfer Reaction in Trans-3-(4-Monomethylamino-Phenyl)-Acrylic Acid: Spectroscopic Measurement and Theoretical Calculations J. Photochem. Photobiol. A: Chem. 181 246 256 10.1016/j.jphotochem.2005.12.004 1:CAS:528:DC%2BD28Xmt1ajtb4%3D
39. C Jia S-X Liu C Tanner C Leiggener A Neels L Sanguinet E Levillain S Leutwyler A Hauser S Decurtins 2007 An Experimental and Computational Study on Intramolecular Charge Transfer: A Tetrathiafulvalene-Fused Dipyridophenazine Molecule Chem. Eur. J. 13 3804 3812 10.1002/chem.200601561 1:CAS:528: DC%2BD2sXlsVGlt7w%3D (Pubitemid 46925636)
40. SV Rosokha JK Kochi 2008 Fresh Look at Electron-Transfer Mechanisms Via the Donor/Acceptor Bindings in the Critical Encounter Complex Acc. Chem. Res. 41 641 653 10.1021/ar700256a 1:CAS:528:DC%2BD1cXktFSgsro%3D
41. AM Brouwer FW Langkilde K Bajdor R Wilbrandt 1994 Through-Bond Interaction in the Radical Cation of N, N-Dimethylpiperazine. Resonance Raman Spectroscopy and Quantum Chemical Calculations Chem. Phys. Lett. 225 386 390 10.1016/0009-2614(94)87099-3 1:CAS:528:DyaK2cXmtFKht7g%3D
42. AM Brouwer 1997 Ab Initio Study of the Structures and Vibrational Spectra of Some Diamine Radical Cations J. Phys. Chem. A 101 3626 3633 10.1021/jp970142o 1:CAS:528:DyaK2sXislKgtb4%3D (Pubitemid 127573264)