Generation of arylnitrenium ions by nitro-reduction and gas-phase synthesis of N-heterocycles

Journal of the American Society for Mass Spectrometry

Volumn 15, Issue 11, 2004, Pages 1675-1688

  Chen, Hao ^a   Chen, Huanwen ^a   Cooks, R Graham ^a   Bagheri, Habib ^b  

^a PURDUE UNIVERSITY   (United States)

^b SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL IONIZATION (CI); REGIOSELECTIVITY;

CHEMICAL BONDS; EXPLOSIVES; IONIZATION; MIXTURES; REDUCTION;

IONS;

1,2 DICHLOROETHANE; 1,3 DIOXOLANE DERIVATIVE; AROMATIC NITRO COMPOUND; HETEROCYCLIC COMPOUND; INDOLE; MORPHOLINE DERIVATIVE; NITROBENZENE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COLLISIONALLY ACTIVATED DISSOCIATION; GAS; MASS SPECTROMETRY; REDUCTION; SYNTHESIS;

BENZOXAZINES; CATIONS; ETHYLENE DICHLORIDES; HYDROCARBONS, AROMATIC; INDOLES; NITRO COMPOUNDS; NITROBENZENES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 7244229730     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2004.07.019     Document Type: Article

References (60)

1. P.G. Gassman Nitrenium Ions Acc. Chem. Res. 3 1970 26
2. J.C. Fishbein, R.A. Mcclelland Azide Ion Trapping of the Intermediate in the Bamberger Rearrangement Lifetime of a Free Nitrenium Ion in Aqueous Solution J. Am. Chem. Soc. 109 1987 2824
3. R.A. Mcclelland Flash Photolysis Generation and Reactivities of Carbenium Ions and Nitrenium Ions Tetrahedron 52 1996 6823
4. J.D. Scribner, N.K. Naimy Adducts between the Carcinogen 2-Acetamidophenanthrene and Adenine and Guanine of DNA Cancer Res. 35 1975 1416
5. J.A. Miller Carcinogenesis by Chemicals: An Overview--G. H. A. Clowes Memorial Lecture Cancer Res. 30 1970 559
6. H.J.J. Moonen, J.J. Briede, J.M.S. Van Maanen, J.C.S. Kleinjans, T.M.C.M. De Kok Generation of Free Radicals and Induction of DNA Adducts by Activation of Heterocyclic Aromatic Amines via Different Metabolic Pathways in Vitro Mol. Carcinogen. 35 2002 196
7. 32p-Postlabeling Analyses of DNA in Human Uroepithelial Cells Exposed to Proximate Metabolites of the Environmental Carcinogen 4-Aminobiphenyl Environ. Mol. Mutagen. 39 2002 314
8. + J. Am. Chem. Soc. 116 1994 11626
9. M. Novak, S.A. Kennedy Selective Trapping of N-Acetyl-N-(4-Biphenylyl) Nitrenium and N-Acetyl-N-(2-Fluorenyl)Nitrenium Ions by 2′-Deoxyguanosine in Aqueous Solution J. Am. Chem. Soc. 117 1995 574
10. M. Novak, K. Toth, S. Rajagopal, M. Brooks, L.L. Hott, M. Moslener Reactivity and Selectivity of the N-Acetyl-Glu-P-1, N-Acetyl-Glu-P-2, N-Acetyl-Meiqx, and N-Acetyl-Iqx Nitrenium Ions Comparison to Carbocyclic N-Arylnitrenium Ions J. Am. Chem. Soc. 124 2002 7972
11. S. Srivastava, J.P. Toscano, R.J. Moran, D.E. Falvey Experimental Confirmation of the Iminocyclohexadienyl Cation-Like Structure of Arylnitrenium Ions Time-Resolved IR Studies of Diphenylnitrenium Ion J. Am. Chem. Soc. 119 1997 11552
12. P.G. Gassman, G.A. Campbell Mechanism of the Chlorination of Anilines and Related Aromatic Amines Involvement of Nitrenium Ions J. Am. Chem. Soc. 93 1971 2567
13. P.G. Gassman, G.A. Campbell, R.C. Frederick Chemistry of Nitrenium Ions XXI. Nucleophilic Aromatic Substitution of Anilines via Aryl Nitrenium Ions (Anilenium Ions) J. Am. Chem. Soc. 94 1972 3884
14. D. Ren, R.A. Mcclelland Carbocation-Like Reactivity Patterns in X′-Substituted-4-Biphenylylnitrenium Ions Can. J. Chem. 76 1998 78
15. S. Srivastava, P.H. Ruane, J.P. Toscano, M.B. Sullivan, C.J. Cramer, D. Chiapperino, E.C. Reed, D.E. Falvey Structures of Reactive Nitrenium Ions Time-Resolved Infrared Laser Flash Photolysis and Computational Studies of Substituted N-Methyl-N-Arylnitrenium Ions J. Am. Chem. Soc. 122 2000 8271
16. J.M. Parks, G.P. Ford, C.J. Cramer Quantum Chemical Characterization of the Reactions of Guanine with the Phenylnitrenium Ion J. Org. Chem. 66 2001 8997
17. Campbell, J. L.; Kenttämaa, H. I. Reactions of the Phenylnitrenium Ion in the Gas Phase: Observing Electronic Reactivity Leading to Carcinogenic Activity, unpublished results.
18. R.A. Abramovitch, K. Evertz, G. Huttner, H.J. Gibson, H.G. Weems Thermolysis of 1-(N-Acetyl-N-Arylamino)-2,4,6-Triphenylpyridinium Tetrafluoroborates A New Source of Arylnitrenium Ions J. Chem. Soc. Chem. Commun. 4 1988 325
19. R.A. Abramovitch, Q. Shi Photolytic Generation of N-Acylnitrenium Ions under Neutral Conditions Synthesis of Polycyclic Lactams Heterocycles 37 1994 1463
20. H. Takeuchi, S. Hayakawa, H. Murai Singlet Stabilization of Parent Nitrenium Ion J. Chem. Soc. Chem. Commun. 19 1988 1287
21. H. Takeuchi, S. Hayakawa, T. Tanahashi, A. Kobayashi, T. Adachi, D. Higuchi Novel Generation of Parent, Alkyl, Dialkyl, and Alicyclic Nitrenium Ions in Photolyses of Pyridinium, Quinolinium, Bipyridinium, and Phenanthrolinium Salts and Aromatic N-Substitution by Nitrenium Ions J. Chem. Soc. Perkin 2 6 1991 847
22. 2+ The Role of the Singlet and Triplet States in Its Reactions with Water, Methanol, and Hydrocarbons J. Org. Chem. 64 1999 5853
23. R.J. Moran, D.E. Falvey Photogenerated Diarylnitrenium Ions Laser Flash Photolysis and Product Studies on Diphenylnitrenium Ion Generated from Photolysis of 1-(N,N-Diphenylamino)Pyridinium Ions J. Am. Chem. Soc. 118 1996 8965
24. R.A. Mcclelland, P.A. Davidse, G. Hadzialic Electron-Deficient Strong Bases. Generation of the 4-Biphenylyl- and 2-Fluorenylnitrenium Ions by Nitrene Protonation in Water J. Am. Chem. Soc. 117 1995 4173
25. R.A. Mcclelland, A. Ahmad, A.P. Dicks, V.E. Licence Spectroscopic Characterization of the Initial C8 Intermediate in the Reaction of the 2-Fluorenylnitrenium Ion with 2′-Deoxyguanosine J. Am. Chem. Soc. 121 1999 3303
26. S.A. Kennedy, M. Novak, B.A. Kolb Reactions of Ester Derivatives of Carcinogenic N-(4-Biphenylyl)Hydroxylamine and the Corresponding Hydroxamic Acid with Purine Nucleosides J. Am. Chem. Soc. 119 1997 7654
27. U. Svanholm, V.D. Parker Chemistry of the Dianisylnitrenium Ion. Stable Protonated Nitrenium Ions J. Am. Chem. Soc. 96 1974 1234
28. D. Serve Chemistry of Electrogenerated Diarylnitrenium Ions. Absorption Spectra of Stable Protonated Nitrenium Ions J. Am. Chem. Soc. 97 1975 432
29. M. Attina, F. Cacace, G.D. Petris Gas Phase Protonation of Alkyl and Phenyl Azides Int. J. Mass Spectrom. Ion Processes 90 1989 263
30. N. Kasthurikrishnan, R.G. Cooks, M.J. Thompson Sampling of Aryldiazonium, Anilino, and Aryl Radicals by Membrane Introduction Mass Spectrometry Thermolysis of Aromatic Diazoamino Compounds J. Am. Soc. Mass Spectrom. 9 1998 234
31. H. Chen, X. Zheng, P. Yang, R.G. Cooks Reduction of Nitroaromatics to Arylnitrenium Ions by Vinyl Halide Cations Chem. Commun. 6 2004 688
32. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, J.A. Pople Gaussian 98, Revision A7 1998 Gaussian, Inc Pittsburgh, PA
33. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, 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, 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 2003 2003 Gaussian, Inc Pittsburgh, PA
34. A.A. Sabino, E.C. Meurer, M.N. Eberlin Ionic Transacetalization with Acylium Ions A Class-Selective and Structurally Diagnostic Reaction for Cyclic Acetals Performed under Unique Electrospray and Atmospheric Pressure Chemical Ionization In-Source Ion-Molecule Reaction Conditions Anal. Chem. 75 2003 4701
35. T.L. Kruger, R. Flammang, J.F. Litton, R.G. Cooks Protonation, Ethylation, and Allylation of Substituted Nitrobenzenes in the Gas Phase. A Study by Ion Kinetic Energy Spectrometry and Chemical Ionization Tetrahedron Lett. 50 1976 4555
36. B. Robinson Studies on the Fischer Indole Synthesis Chem. Rev. 69 1969 227
37. P.G. Gassman, T.J.V. Bergen, D.P. Gilbert, B.W. Cue General Method for the Synthesis of Indoles J. Am. Chem. Soc. 96 1974 5495
38. V.G. Granik, V.M. Lyubchanskaya, T.I. Mukhanova Nenitzescu Reaction Khimiko-Farmatsevticheskii Zhurnal 27 1993 37
39. G.L. Glish, R.G. Cooks The Fischer Indole Synthesis and Pinacol Rearrangement in the Mass Spectrometer J. Am. Chem. Soc. 100 1978 6720
40. G. Sindona, N. Uccella, D. Stahl Reaction Mechanisms of Gaseous Organic Ions. Part 22. Structure and Reactivity of Protonated Indole in the Gas Phase by MS/MS Int. J. Mass Spectrom. Ion Processes 63 1985 49
41. R.A. Mcclelland, M.J. Kahley, P.A. Davidse Reactivity of the 4-Biphenyl and 2-Fluorenylnitrenium Ions with Heterocyclic and Carbon Nucleophiles J. Phys. Org. Chem. 9 1996 355
42. S.J. Blanksby, J.H. Bowie Construction of Interstellar Cumulenes and Heterocumulenes Mass Spectrometric Studies Mass Spectrom. Rev. 18 1999 131
43. T.D. Burns, T.G. Spence, M.A. Mooney, L.A. Posey Electrospray Ionization of Divalent Transition Metal Ion Bipyridine Complexes Spectroscopic Evidence for Preparation of Solution Analogs in the Gas Phase Chem. Phys. Lett. 258 1996 669
44. C.H. Depuy Understanding Organic Gas-Phase Anion Molecule Reactions J. Org. Chem. 67 2002 2393
45. C.L. Johlman, R.L. White, D.T. Sawyer, C.L. Wilkins Gas-Phase Hydrolysis of Phenyl Acetate and Phenyl Benzoate by Superoxide Ion J. Am. Chem. Soc. 105 1983 2091
46. M. Sainsbury Oxazines, Thiazines and Their Benzoderivatives in Comprehensive Heterocyclic Chemistry 3 1984 995
47. Y. Sugimoto, T. Otani, S. Oie, K. Wierzba, Y. Yamada Mechanism of Action of a New Macromolecular Antitumor Antibiotic, C-1027 J. Antibiot. 43 1990 417
48. T. Fukuda, M. Setoguchi, K. Inaba, H. Shoji, T. Tahara The Antiemetic Profile of Y-25130, a New Selective 5-Ht3 Receptor Antagonist Eur. J. Pharmacol. 196 1991 299
49. T. Hirata, H. Saito, H. Tomioka, K. Sato, J. Jidoi, K. Hosoe, T. Hidaka In Vitro and in Vivo Activities of the Benzoxazinorifamycin Krm-1648 Against Mycobacterium tuberculosis Antimicrob. Agents Chemother. 39 1995 2295
50. H. Matsuoka, N. Ohi, M. Mihara, H. Suzuki, K. Miyamoto, N. Maruyama, K. Tsuji, N. Kato, T. Akimoto, Y. Takeda, K. Yano, T. Kuroti Antirheumatic Agents Novel Methotrexate Derivatives Bearing a Benzoxazine or Benzothiazine Moiety J. Med. Chem. 40 1997 105
51. X. Zheng, W.A. Tao, R.G. Cooks Eberlin Reaction of Arenesulfenylium Cations with Cyclic Acetals and Ketals Ring Contraction and Cycloreversion J. Chem. Soc. Perkin 2 3 2001 350
52. M.N. Eberlin, R.G. Cooks Gas-Phase Oxirane to Acylium Ions on Reaction with 1,3-Dioxolanes Elucidated by Tandem and Triple Stage Mass Spectrometric Experiments Org. Mass Spectrom. 28 1993 679
53. F. Wang, S. Ma, W.A. Tao, R.G. Cooks Replacement of CO by PO in Cyclic Acetals and Ketals Angew. Chem., Int. Ed. Engl. 38 1999 386
54. W.A. Tao, X. Zheng, R.G. Cooks Synthesis of B,N,O-Containing Heterocycles via Eberlin Reaction of Dimethylamino Borinium Ion with Cyclic Acetals and Ketals J. Mass Spectrom. 35 2000 1215
55. H. Chen, X. Zheng, R.G. Cooks Ketalization of Phosphonium Ions by 1,4-Dioxane Selective Detection of the Chemical Warfare Agent Simulant Dmmp in Mixtures Using Ion/Molecule Reactions J. Am. Soc. Mass Spectrom. 14 2003 182 188
56. Cooks, R. G. The Eberlin Reaction: Ionic Transacetalization in the Gas Phase, unpublished results.
57. A. Colorado, J. Brodbelt Class-Selective Collisionally Activated Dissociation/Ion-Molecule Reactions of 4-Quinolone Antibiotics Anal. Chem. 66 1994 2330
58. J. Brodbelt Analytical Applications of Ion/Molecule Reactions Mass Spectrom. Rev. 16 1997 91
59. E.C. Meurer, H. Chen, L.S. Riter, I. Cotte-Rodriguez, M.N. Eberlin, R.G. Cooks Gas-Phase Reactions for Selective Detection of the Explosives TNT and RDX Chem. Commun. 1 2004 40
60. H. Chen, H. Chen, R.G. Cooks Meisenheimer Complexes Bonded at Carbon and at Oxygen in the Gas Phase J. Am. Soc. Mass Spectrom. 15 2004 998 1004