Effect of substituents and protonation on the mechanism of 1,3-dipolar retro-cycloaddition reaction of pyrrolidino[60]- and [70]fullerenes

Journal of Mass Spectrometry

Volumn 46, Issue 10, 2011, Pages 1016-1029

  Maroto, Enrique ^a   Filippone, Salvatore ^a   Martín Domenech, Angel ^a   Suárez, Margarita ^b   Martín, Nazario ^a,c   Martínez Alvarez, Roberto ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSITY OF HAVANA   (Cuba)

^c INSTITUTO MADRILEÑO DE ESTUDIOS AVANZADOS EN NANOCIENCIA IMDEA NANOCIENCIA   (Spain)

Author keywords

electrospray ionization; even electron rule; fragmentation of pyrrolidinofullerenes; pyrrolidinofullerenes; retro cycloaddition reaction

Indexed keywords

[60]- AND [70]FULLERENES; COLLISION-INDUCED DISSOCIATION; CONDENSED PHASE; CYCLOREVERSION PROCESS; CYCLOREVERSION REACTIONS; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; EVEN-ELECTRON IONS; EVEN-ELECTRON RULE; FOURIER TRANSFORM ION CYCLOTRON RESONANCE; FRAGMENT IONS; GASPHASE; HETEROCYCLIC MOIETIES; HYDROGEN SHIFTS; IONIC SPECIES; MASS SPECTRA; METHANOFULLERENES; MOLECULES AND IONS; MULTIPLE BONDS; NEUTRAL MOLECULES; NH GROUPS; NITROGEN ATOM; PH CONDITION; POSITIVE MODE; PROTONATED; PROTONATED MOLECULES; PYRROLIDINE RINGS; PYRROLIDINOFULLERENES; QUADRUPOLE ION TRAPS; RADICAL ANIONS; RETRO-CYCLOADDITION REACTION; THERMAL REACTIONS;

CHEMICAL DETECTION; CYCLOADDITION; ELECTRONS; FOURIER TRANSFORMS; FULLERENES; IONIZATION OF GASES; MASS SPECTROMETERS; MASS SPECTROMETRY; MOLECULES; NEGATIVE IONS; NITROGEN; PROTONATION;

ELECTROSPRAY IONIZATION;

ANION; FULLERENE DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROGEN; NITROGEN; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL BOND; COLLISIONALLY ACTIVATED DISSOCIATION; CYCLOADDITION; ELECTRON; ELECTROSPRAY MASS SPECTROMETRY; FRAGMENTATION REACTION; GAS; ION CYCLOTRON RESONANCE MASS SPECTROMETRY; ION TRAP MASS SPECTROMETRY; PH; PRIORITY JOURNAL; PROTON TRANSPORT;

EID: 80054795451     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1983     Document Type: Article

References (78)

1. 60 Buckminsterfullerene. Nature 1985, 318, 162-163.
2. A. Hirsch, M. Brettreich,. The Chemistry of Fullerenes, Wiley-VCH: Weinheim, Germany, 2005.
3. N. Martín,. New challenges in fullerene chemistry. Chem. Commun. 2006, 2093-2104. (Pubitemid 43844068)
4. Fullerenes. Principles and Applications, F. Langa, and, J.-F. Nierengarten, (Eds). RSC: Cambridge, UK, 2007.
5. Fullerenes: From Synthesis to Optoelectronic Properties, D. M. Guldi, and, N. Martín, (Eds). Kluver Academic: Dordrech, The Netherlands, 2002.
6. L. Sánchez, R. Otero, J. M. Gallego, R. Miranda, N. Martín,. Ordering fullerenes at the nanometer scale on solid surfaces. Chem. Rev. 2009, 109, 2081-2091.
7. J. L. Delgado, P. A. Bouit, S. Fillipone, M. A. Herranz, N. Martín,. Organic photovoltaics: a chemical approach. Chem. Commun. 2010, 46, 4853-4865.
8. D. Pantorotto, N. Tagmatarchis, A. Bianco, M. Prato,. Synthesis and biological properties of fullerene-containing amino acids and peptides. Mini-Rev. Med. Chem. 2004, 4, 805-814. (Pubitemid 39149480)
9. R. Bakty, R. M. Vallant, M. Najam-Ul-Haq, M. Rainer, Z. Szabo, C. W. Huck, G. Bonn,. Medicinal applications of fullerenes. Int. J. Nanomed. 2007, 2, 639-649.
10. N. Martín, M. Altable, S. Filippone, A. Martín-Domenech,. New reactions in fullerene chemistry. Synlett 2007, 3077-3095.
11. S. Filippone, E. Maroto, A. Martín-Domenech, M. Suárez, N. Martín,. An efficient approach to chiral fullerene derivatives by catalytic enantioselective 1,3-dipolar cycloaddition. Nat. Chem. 2009, 1, 578-582.
12. F. W. McLafferty,. Mass spectrometry across the sciences. Proc. Natl. Acad. Sci. USA. 2008, 105, 18088-18089.
13. R. Bakhtiar, C. E. A. Hop,. Unraveling seemingly complex chemistry of reactions using electrospray ionization mass spectrometry. J. Phys. Org. Chem. 1999, 12, 511-527. (Pubitemid 129659141)
14. S. R. Wilson, Y. Wu,. Detection of methoxylated anions of fullerenes by electrospray ionization mass spectrometry. J. Am. Chem. Soc. 1993, 115, 10334-10337.
15. - by electrospary ionization. Rapid Commun. Mass Spectrom. 1992, 6, 254-256.
16. S. Fujimaki, I. Kudaka, T. Sato, K. Hiraoka, H. Shinohara, Y. Saito, K. Nojima,. Application of electrospray ionization to the observation of higher fullerene anions. Rapid Commun. Mass Spectrom. 1993, 7, 1077-1081.
17. S. R. Stephen, Y. Wu,. Applications of electrospray ionization mass spectrometry to neutral organic molecules including fullerenes. J. Am. Soc. Mass Spectrom. 1993, 4, 596-603.
18. A. Dupont, J.-P. Gisselbrecht, E. Leize, L. Wagner, A. Van Dorsselaer,. Electrospray mass spectrometry of electrochemically ionized molecules: application to the study of fullerenes. Tetrahedron Lett. 1994, 35, 6083-6086.
19. V. Kozlovski, V. Brusov, I. Sulimenkov, A. Pikhtelev, A. Dodonov,. Novel experiment arrangement developed for direct fullerene analysis by electrospray time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 2004, 18, 780-785.
20. 24. J. Am. Chem. Soc. 2004, 126, 1618-1619.
21. I. E. Kareev, V. P. Bubnov, E. E. Laukhina, A. F. Dodonov, V. I. Kozlovski, E. B. Yagubskii,. Experimental evidence in support of the formation of anionic endohedral metallofullerenes during their extraction with N,N-dimethylformamide. Fullerenes, Nanotubes, Carbon Nanostruct. 2004, 12, 65-69. (Pubitemid 41341939)
22. 6 with N-substituted piperazines. Tetrahedron 2006, 62, 10147-10151. (Pubitemid 44363098)
23. J. Hua, F. Meng, F. Ding, F. Li, H. Tian,. Novel soluble and thermally-stable fullerene dyad containing perylene. J. Mater. Chem. 2004, 14, 1849-1853.
24. 60. Tetrahedron 2007, 63, 7070-7076. (Pubitemid 46891524)
25. C. W. Isaacson, C. Usenko, R. L. Tanguay, J. A. Field,. Quantification of fullerenes by LC/ESI-MS and its application to in vivo toxicity assays. Anal. Chem. 2007, 79, 9091-9097. (Pubitemid 350231720)
26. 10. J. Am. Chem. Soc. 2010, 132, 6443-6462.
27. L. Nebhani, C. Barner-Kowolik,. Functionalization of fullerenes with cyclopentadienyl and antracenyl capped polymeric building blocks via Diels-Alder chemistry. Macromol. Rapid Commun. 2010, 31, 1298-1305.
28. C. Gasbarra, S. Guernelli, S. Boncompagni, G. Angelini, G. Siani, P. Di Maria, A. Fontana,. Fine-tunninf of POPC liposomal leakage by the use of β-cyclodextrin and several hydrophobic guests. J. Liposome Res. 2010, 20, 202-210.
29. J.-F. Nierengarten, J. Iehl, V. Oerthel, M. Holler, B. M. Illescas, A. Muñoz, N. Martín, J. Rojo, M. Sánchez-Navarro, S. Cecioni, S. Vidal, K. Buffet, M. Durka, S. P. Vincent,. Fullerene sugar balls. Chem. Commun. 2010, 46, 3860-3862.
30. 10 dyads. Chem. Eur. J. 2010, 16, 5343-5353.
31. 60 fullerene. Tetrahedron Lett. 1995, 36, 2457-2458.
32. 60 cycloadducts. Synthesis and mass spectrometric characterization. Synth. Met. 1996, 77, 93-95. (Pubitemid 126341296)
33. 60-pyrimidine derivatives. J. Mass Spectrom. 2009, 44, 911-919.
34. E. Nakamura, H. Isobe, N. Tomita, M. Sawamura, S. Jinno, H. Okayama,. Functionalized fullerene as an artificial vector for transfection. Angew. Chem. Int. Ed. 2000, 39, 4254-4257.
35. S. Bosi, T. Da Ros, G. Spalluto, M. Prato,. Fullerene derivatives: an attractive tool for biological applications. Eur. J. Med. Chem. 2003, 38, 913-923. (Pubitemid 37455402)
36. F. Giacalone, N. Martín,. Fullerene polymers: synthesis and properties. Chem. Rev. 2006, 106, 5136-5190. (Pubitemid 46099390)
37. 70) for energy harvesting. Chem. Eur. J. 2009, 48, 13474-13482.
38. J. L. Delgado, P.-A. Bouit, S. Filippone, M. A. Herranz, N. Martín,. Organic photovoltaics: a chemical approach. Chem. Commun. 2010, 46, 4853-4865.
39. C. Villegas, E. Krokos, P.-A. Bouit, J. L. Delgado, D. M. Guldi, N. Martín,. Efficient light harvesting anionic heptamethine cyanine-[60] and [70]fullerene hybrids. Energy Environ. Sci. 2011, 4, 679-684.
40. 70. Angew. Chem. Int. Ed. 2011, 50, 6060-6064.
41. P. A. Troshin, S. I. Troyanov, G. N. Boiko, R. N. Lyubovskaya, A. N. Lapshin, N. F. Goldshleger,. Efficient 2,3-cycloaddition approach to synthesis of pyridinyl based [60]fullerene ligands. Fullerenes, Nanotubes, Carbon Nanostruct. 2004, 12, 413-419.
42. S.-H. Wu, W.-Q. Sun, D.-W. Zhang, L.-H. Shu, H.-M. Wu, J.-F. Xu, X.-F. Lao,. 1,3-Dipolar cycloaddition of several azomethine ylides to [60]fullerene: synthesis of derivatives of 2′,5′-dihydro-1′H- pyrrolo[3′,4′:1,2][60]fullerene. J. Chem. Soc. Perkin Trans. 1 1998, 1733-1738. (Pubitemid 128756920)
43. U. M. Fernández-Paniagua, B. Illescas, N. Martín, C. Seoane, P. de la Cruz, A. de la Hoz, F. Langa,. Thermal and microwave-assisted synthesis of Diels-Alder adducts of [60]fullerene with 2,3- pyrazinoquinodimethanes: characterization and electrochemical properties. J. Org. Chem. 1997, 62, 3705-3710. (Pubitemid 127492976)
44. B. González, A. Herrera, B. Illescas, N. Martín, R. Martínez, F. Moreno, L. Sánchez, A. Sánchez,. Diels-Alder cycloadducts of [60]fullerene with pyrimidine o-quinodimethanes. J. Org. Chem. 1998, 63, 6807-6813.
45. J. L. Segura, N. Martín,. o-Quinodimethanes: efficient intermediates in organic synthesis. Chem. Rev. 1999, 99, 3199-3246. (Pubitemid 129583052)
46. J.-H. Liu, A-T- Wu., M.-H. Wu, C-W- Cheng,. The synthesis of pyrazino-containing sultines and their applications in Diels-Alder reactions with electron poor olefins and [60]fullerene. J. Org. Chem. 2000, 65, 3395-3403. (Pubitemid 30346793)
47. R. F. Enes, A. C. Tomé, J. A. S. Cavaleiro,. Synthesis of [60]fullerene-based α-amino acid derivatives. Tetrahedron 2005, 61, 1423-1431. (Pubitemid 40139135)
48. 60. Rapid Commun. Mass Spectrom. 1998, 12, 568-570. (Pubitemid 28202984)
49. 1H NMR dynamic strudy. Tetrahedron 2009, 65, 5817-5823.
50. M. Prato, M. Maggini,. Fulleropyrrolidines: a family of full-fledged fullerene derivatives. Acc. Chem. Res. 1998, 31, 519-526. (Pubitemid 128473644)
51. N. Tagmatarchis, M. Prato,. The addition of azomethine ylides to [60]fullerene leading to fulleropyrrolidines. Synlett 2003, 768-779. (Pubitemid 36577752)
52. 70 under microwave irradiation. J. Org. Chem. 2000, 65, 2499-2507. (Pubitemid 30235820)
53. N. Martín, M. Altable, S. Filippone, A. Martín-Domenech, R. Martínez-Alvarez, M. Suárez, M. E. Plonska-Brzezinska, O. Lukoyanova, L. Echegoyen,. Highly efficient retro-cycloaddition reaction of isoxazolino[4,5:1,2][60]- and [70]fullerenes. J. Org. Chem. 2007, 72, 3840-3846. (Pubitemid 46762471)
54. J. L. Delgado, S. Filippone, A. Martín-Domenech, M. Altable, E. Maroto, F. Langa, N. Martín, R. Martínez-Alvarez,. Mass Spectrometry studies of the retro-cycloaddition reaction of pyrrolidino and 2-pyrazolinofullerene derivatives under negative ESI conditions. J. Am. Soc. Mass Spectrom. 2011, 22, 557-567.
55. 60 derivatives: high resolution mass measurement and molecular ion gas-phase reactivity. Rapid Commun. Mass Spectrom. 2001, 15, 1708-1712. (Pubitemid 32906417)
56. 60 adducts by ESI/MS: evidence for dimerized cation-radicals. J. Mass Spectrom. 2002, 37, 1081-1085. (Pubitemid 35238258)
57. J.-F. Greisch, E. D. Pauw,. Mass spectrometric characterization of 3′-imino[60]fulleryl-3′-deoxythymidine by collision-induced dissociation. J. Mass Spectrom. 2007, 42, 304-311. (Pubitemid 46426675)
58. S. W. McElvany, J. H. Callahan,. Chemical ionization of fullerenes. J. Phys. Chem. 1991, 95, 6186-6191.
59. P. A. Troshin, A. S. Peregudov, S. M. Peregudova, R. M. Lyubovskaya,. Highly regio- and stereselective [2 + 3]cycloadditions of azomethine ylides to [70]fullerene. Eur. J. Org. Chem. 2007, 5861-5866.
60. N. Martín, M. Altable, S. Filippone, A. Martín-Domenech, L. Echegoyen, C. M. Cardona,. Retro-cycloaddition reaction of pyrrolidinofullerenes. Angew. Chem. Int. Ed. 2006, 45, 110-114. (Pubitemid 43008375)
61. O. Lukoyanova, C. M. Cardona, M. Altable, S. Filippone, A. Martín-Domenech, N. Martín, L. Echegoyen,. Selective electrochemical retro-cycloaddition of pyrrolidinofullerenes. Angew. Chem. Int. Ed. 2006, 45, 7430-7433.
62. J. H. Gross,. Mass Spectrometry. Springer: New-york, 2004, 321.
63. II and reaction mechanism studies by detection of transient radical cations. Eur. J. Org. Chem. 2007, 5162-5174.
64. K. Levsen, H. M. Scheibel, J. K. Terlouw, K. J. Elend, A. Preiss, H. Thiele, A. Ingendoh,. Even-electron ions: a systematic study of the neutral species lost in the dissociation of quasi-molecular ions. J. Mass Spectrom. 2007, 42, 1024-1044. (Pubitemid 47255454)
65. E. M. Thurman, I. Ferrer, O. J. Pozo, J. V. Sancho, F. Hernández,. The even-electron rule in electrospray mass spectra of pesticides. Rapid Commun. Mass Spectrom. 2007, 21, 3855-3868. (Pubitemid 350220694)
66. Y. Cai, Z. Mo, N. S. Rannulu, B. Guan, S. Kannupal, B. C. Gibb, R. B. Cole,. 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. 2010, 45, 235-240.
67. A. G. Brenton, A. R. Godfrey,. Accurate mass measurement: terminology and treatment of data. J. Am. Soc. Mass Spectrom. 2010, 21, 1821-1835.
68. A. Bagno, S. Claeson, M. Maggini, M. L. Martini, M. Prato, G. Scorrano,. [60]Fullerene as a substituent. Chem. Eur. J. 2002, 8, 1015-1023. (Pubitemid 34250978)
69. I. D. Petsalakis, N. Tagmatarchis, G. Theodorakopoulos,. Theoretical study of fulleropyrrolidines by density functional and time-dependent density functional theory. J. Phys. Chem. C 2007, 111, 14139-14149. (Pubitemid 47548405)
70. M. Suárez, Y. Verdecia, B. Illescas, R. Martínez-Alvarez, A. Alvarez, E. Ochoa, C. Seoane, N. Kayali, N. Martín,. Synthesis and study of novel fulleropyrrolidines bearing biologically active 1,4-dihydropyridines. Tetrahedron 2003, 59, 9179-9186. (Pubitemid 37329567)
71. B. Illescas, R. Martínez-Alvarez, J. Fernández-Gadea, N. Martín,. Synthesis of water soluble fulleropyrrodines bearing biologically active piperazines. Tetrahedron 2003, 59, 6569-6577. (Pubitemid 36930143)
72. O. Timofeev, M. M. Zhu, M. L. Gross,. Information for proteomics: ESI-MS titration by sodium ions gives the number of carboxylate groups in peptides. Int. J. Mass Spectrom. 2004, 231, 113-117.
73. T. Solouki, R. C. Fort Jr., A. Alomary, A. Fattahi,. Gas phase hydrogen deuterium exchange reactions of a model peptide: FT-ICR and computational analyses of metal induced conformational mutations. J. Am. Soc. Mass Spectrom. 2001, 12, 1272-1285. (Pubitemid 34555389)
74. 3: exchange kinetics do not reflect parent ion structures. J. Am. Chem. Soc. 2004, 126, 6485-6490. (Pubitemid 38657072)
75. 1(pyrr) phosphazene. J. Org. Chem. 2002, 67, 1873-1881. (Pubitemid 34246581)
76. a units: unification of different basicity scales. J. Org. Chem. 2005, 70, 1019-1028. (Pubitemid 40189516)
77. S. Filippone, M. Izquierdo, A. Martín-Domenech, S. Osuna, M. Solà, N. Martín,. On the mechanism of the termal retrocycloaddition of pyrrolidinofullerenes (retro-Prato reaction). Chem. Eur. J. 2008, 14, 5198-5206.
78. A. Kütt, T. Rodima, J. Saame, E. Raamat, V. Mäemets, I. Kaljurand, I. A. Koppel, R. Y. Garlyauskayte, Y. L. Yagupolskii, L. M. Yagupolskii, E. Bernhardt, H. Willner, I. Leito,. Equilibrium acidities of superacids. J. Org. Chem. 2011, 76, 391-395.