Gas Phase Fullerene Anions Hydrogenation by Methanol Followed by IRMPA Dehydrogenation

[en] The characterization in the gas phase of the mechanisms responsible for hydride formation can
contribute to the development of new materials for hydrogen storage. The present work
provides evidence of a hydrogenation-dehydrogenation catalytic cycle for C60 anions in the
gas phase using methanol vapor at room temperature as hydrogen donor.

Research Center/Unit :

Département de Chimie

Disciplines :

Chemistry

Author, co-author :

Greisch, Jean-François ; Université de Liège - ULiège > Département de chimie (sciences) > GIGA-R : Laboratoire de spectrométrie de masse (L.S.M.)

Leyh, Bernard ; Université de Liège - ULiège > Département de chimie (sciences) > Laboratoire de dynamique moléculaire

Remacle, Françoise ; Université de Liège - ULiège > Département de chimie (sciences) > Laboratoire de chimie physique théorique

De Pauw, Edwin ; Université de Liège - ULiège > Département de chimie (sciences) > GIGA-R : Laboratoire de spectrométrie de masse (L.S.M.)

Language :

English

Title :

Gas Phase Fullerene Anions Hydrogenation by Methanol Followed by IRMPA Dehydrogenation

Publication date :

2010

Journal title :

Journal of the American Society for Mass Spectrometry

ISSN :

1044-0305

eISSN :

1879-1123

Publisher :

Elsevier Science, New York, United States - New York

Volume :

Issue :

Pages :

117-126

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

http://www.sciencedirect.com/science/journal/10440305

Funders :

F.R.S.-FNRS - Fonds de la Recherche Scientifique
DGTRE - Région wallonne. Direction générale des Technologies, de la Recherche et de l'Énergie

Available on ORBi :

since 11 January 2010

Statistics

Number of views

213 (1 by ULiège)

Number of downloads

0 (0 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenAlex citations

Bibliography

Chen P., Wu X., and Tan K.L. High H2 Uptake by Alkali-Doped Carbon Nanotubes Under Ambient Pressure and Moderate Temperatures. Science 285 (1999) 91-93
Liu C., Fan Y.Y., Liu M., Cong H.T., Cheng H.M., and Dresselhaus M.S. Hydrogen Storage in Single-Walled Carbon Nanotubes at Room Temperature. Science 286 (1999) 1127-1129
Deluga G.A., Salge J.R., Schmidt L.D., and Verykios X.E. Renewable Hydrogen from Ethanol by Autothermal Reforming. Science 303 (2004) 993-997
Baldé C.P., Hereijgers B.P.C., Bitter J.H., and Jong K.P. Sodium Alanate Nanoparticles-Linking Size to Hydrogen Storage Properties. J. Am. Chem. Soc. 130 (2008) 6761-6765
Sunderlin L.S., Paulino J.A., Chow J., Kahr B., Ben-Amotz D., and Squires R.R. Gas-Phase Reactivity of Fullerene Anions. J. Am. Chem. Soc. 113 (1991) 5489-5490
Javahery G., Petrie S., Wincel H., Wang J., and Bohme D.K. Gas-Phase Reactions of the Buckminsterfullerene Cations C60•+, C602+, C60•3+ with Water, Alcohols, and Ethers. J. Am. Chem. Soc. 115 (1993) 6295-6301
Rüchardt C., Gerst M., Ebenhoch J., Beckhaus H.D., Campbell E.E.B., Tellgmann R., Weiske T., and Pitter S. Transfer Hydrogenation and Deuteration of Buckminsterfullerene C60 by 9,10-Dihydroanthracene and 9,9′,10,10′[D4]Dihydroanthracene. Angew. Chem. Int. Ed. Engl. 32 (1993) 584-586
Talyzin A.V., Tsybin Y.O., Schaub T.M., Mauron P., Shulga Y.M., Züttel A., Sundqvist B., and Marshall A.G. Composition of Hydrofullerene Mixtures Produced by C60 Reaction with Hydrogen Gas Revealed by High-Resolution Mass Spectrometry. J. Phys. Chem. B 109 (2005) 12742-12747
Darwish A.D., Abdul-Sada A.K., Langley G.J., Kroto H.W., Taylor R., and Walton D.R.M. Polyhydrogenation of [60]- and [70]-Fullerenes. J. Chem. Soc. Perkin Trans. 12 (1995) 2359-2365 2
Darwish A.D., Avent A.G., Taylor R., and Walton D.R.M. Structural Characterization of C60H18; a C3v Symmetry Crown. J. Chem. Soc. Perkin Trans. 10 (1996) 2051-2054 2
Vasil'ev Y., Wallis D., Nüchter M., Ondruschka B., Lobach A., and Drewello T. From Major to Minor and Back-a Decisive Assessment of C60H36 with Respect to the Birch Reduction of C60. J. Chem. Soc. Chem. Commun. 14 (2000) 1233-1234
Rogner I., Birkett P., and Campbell E.E.B. Hydrogenated and Chlorinated Fullerenes Detected by "Cooled" Modified Matrix-Assisted Laser Desorption Ionization Mass Spectroscopy (MALDI-MS). Int. J. Mass Spectrom. Ion Processes 156 (1996) 103-108
Talyzin A.V., Tsybin Y.O., Purcell J.M., Schaub T.M., Shulga Y.M., Noréus D., Sato T., Dzwilewski A., Sundqvist B., and Marshall A.G. Reaction of Hydrogen Gas with C60 at Elevated Pressure and Temperature: Hydrogenation and Cage Fragmentation. J. Phys. Chem. A 110 (2006) 8528-8534
Vasil'ev Y., Hirsch A., Taylor R., and Drewello T. Hydrogen Storage on Fullerenes: Hydrogenation of C59N Using C60H36 as the Source of Hydrogen. Chem. Commun. 15 (2004) 1752-1753
Haufler R.E., Conceicao J., Chibante L.P.F., Chai Y., Byrne N.E., Flanagan S., Haley M.M., O'Brien S.C., Pan C., Xiao Z., Billups W.E., Ciufolini M.A., Hauge R.H., Margrave J.L., Wilson L.J., Curl R.F., and Smalley R.E. Efficient Production of C60 (Buckminsterfullerene), C60H36, and the Solvated Buckide Ion. J. Phys. Chem. 94 (1990) 8634-8636
Bank M.R., Dale M.J., Gosney I., Hodgson P.K.G., Jennings R.C.K., Jones A.C., Lecoultre J., Langridge-Smith P.R.R., Maier J.P., Scrivens J.H., Smith M.J.C., Smyth C.J., Taylor A.T., Thorburn P., and Webster A.S. Birch Reduction of C60-a New Appraisal. J. Chem. Soc. Chem. Commun. 14 (1993) 1149-1152
Peera A., Saini R.K., Alemany L.B., Billups W.B., Saunders M., Khong A., Syamala M.S., and Cross R.J. Formation, Isolation, and Spectroscopic Properties of Some Isomers of C60H38, C60H40, C60H42, and C60H44-Analysis of the Effects of the Different Shapes of Various Helium-Containing Hydrogenated Fullerenes on Their 3He Chemical Shifts. Eu. J. Org. Chem. (2003) 4140-4145
Briggs J.B., Montgomery M.N., Silva L.L., and Miller G.P. Facile, Scalable, Regioselective Synthesis of C3v C60H18 Using Organic Polyamines. Org. Lett. 7 (2005) 5553-5555
Kintigh J., Briggs J.B., Letourneau K., and Miller G.P. Fulleranes Produced via Efficient Polyamine Hydrogenations of [60]Fullerene, [70]Fullerene, and Giant Fullerenes. J. Mater. Chem. 17 (2007) 4647-4651
Avent A.G., Darwish A.D., Hemibach D.K., Kroto H.W., Meidine M.F., Parsons J.P., Remars C., Roers R., Ohashi O., Taylor R., and Walton D.R.M. Formation of Hydrides of Fullerene-C60 and Fullerene-C70. J. Chem. Soc. Perkin Trans. 2 1 (1994) 15-22
Henderson C.C., and Cahill P.A. C60H2: Synthesis of the Simplest C60 Hydrocarbon Derivative. Science 259 (1993) 1885-1887
Henderson C.C., Rohlfing C.M., Assink R.A., and Cahill P.A. C60H4: Kinetics and Thermodynamics of Multiple Addition to C60. Angew. Chem. Int. Ed. Engl. 33 (1994) 786-788
Vasil'ev Y.V., Absalimov R.R., Nasibullaev S.K., Lobach A.S., and Drewello T. Formation and Characterization of Long-lived Negative Molecular Ions of C60H18. J. Phys. Chem. A 105 (2001) 661-665
Gerst M., Beckhaus H.D., Rüchardt C., Campbell E.E.B., and Tellgmann R. [7H]Benzanthrene, a Catalyst for the Transfer Hydrogenation of C60 and C70 by 9,10-Dihydroanthracene. Tetrahedron Lett. 34 (1993) 7729-7732
Fukuzumi S., Suenobu T., Kawamura S., Ishida A., and Mikami K. Selective Two-Electron Reduction of C60 by 10-Methyl-9,10-Dihydroacridine via Photoinduced Electron Transfer. J. Chem. Soc. Chem. Commun. 3 (1997) 291-292
Becker L., Evans T., and Bada J.L. Synthesis of C60H2 by Rhodium-Catalyzed Hydrogenation of C60. J. Org. Chem. 58 (1993) 7630-7631
Talyzin A.V., Shulga Y.M., and Jacob A. Comparative Study of Hydrofullerides C60Hx Synthesized by Direct and Catalytic Hydrogenation. App. Phys. A 78 (2004) 1005-1010
Osaki T., Tanaka T., and Tai Y. Hydrogenation of C60 on Alumina-Supported Nickel and Thermal Properties of C60H36. Phys. Chem. Chem. Phys. 1 (1999) 2361-2366
Meier M.S., Corbin P.S., Vance V.K., Clayton M., Mollman M., and Poplawska M. Synthesis of Hydrogenated Fullerenes by Zinc/Acid Reduction. Tetrahedron Lett. 35 (1994) 5789-5792
Darwish A.D., Abdul-Sada A.K., Langley G.J., Kroto H.W., Taylor R., and Walton D.R.M. Polyhydrogenation of [60]- and [70]Fullerenes with Zn/HCl and Zn/DCl. Synth. Met. 77 (1996) 303-307
Meier M.S., Weedon B.R., and Spielmann H.P. Synthesis and Isolation of One Isomer of C60H6. J. Am. Chem. Soc. 118 (1996) 11682-11683
Bergosh R.G., Meier M.S., Cooke J.A.L., Spielmann H.P., and Weedon B.R. Dissolving Metal Reductions of Fullerenes. J. Org. Chem. 62 (1997) 7667-7672
Meier M.S., Spielmann H.P., Haddon R.C., Bergosh R.G., Gallagher M.E., Hamon M.A., and Weeden B.R. Reactivity, Spectroscopy, and Structure of Reduced Fullerenes. Carbon 38 (2000) 1535-1538
Ballenweg S., Gleiter R., and Krätschmer W. Hydrogenation of Buckminsterfullerene C60 via Hydrozirconation: A New Way to Organofullerenes. Tetrahedron Lett. 34 (1993) 3737-3740
Attalla M.L., Vassalo A.M., Tattam B.N., and Hana J.V. Preparation of Hydrofullerenes by Hydrogen Radical Induced Hydrogenation. J. Phys. Chem. 97 (1993) 6329-6331
Cliffel D.E., and Bard A.J. Electrochemical Studies of the Protonation of C60- and C60(2-). J. Phys. Chem. 98 (1994) 8140-8143
Niyazymbetov M.E., Evans D.H., Lerke S.A., Cahill P.A., and Henderson C.C. Study of Acid-Base and Redox Equilibria for the C60/C60H2 System in Dimethyl Sulfoxide Solvent. J. Phys. Chem. 98 (1994) 13093-13098
Nozu R., and Matsumoto O. Hydrogenation of C60 by Electrolysis of KOH-H2O Solution. J. Electrochem. Soc. 143 (1996) 1919-1923
Mandrus D., Kele M., Hettich R.L., Guiochon G., Sales B.C., and Boatner L.A. Sonochemical Synthesis of C60H. J. Phys. Chem. B 101 (1997) 123-128
Jin C., Hettich R., Compton R., Joyce D., Blencoe J., and Buch T. Direct Solid-Phase Hydrogenation of Fullerenes. J. Phys. Chem. 98 (1994) 4215-4217
Vieira S.M.C., Ahmed W., Birkett P.R., and Rego C.A. Hydrogenation of [60]Fullerene Using a Novel Chemical Vapor Modification (CVM) Method. Chem. Phys. Lett. 347 (2001) 355-360
Wågberg T., Johnels D., Peera A., Hedenstroem M., Shulga Y.M., Tsybin Y.O., Purcell J.M., Marshall A.G., Noreus D., Sato T., and Talyzin A.V. Selective Synthesis of the C3v Isomer of C60H18. Org. Lett. 7 (2005) 5557-5560
Talyzin A.V., Dzwilewski A., Sundqvist B., Tsybin Y.O., Purcell J.M., Marshall A.G., Shulga Y.M., McCammon C., and Dubrovinsky L. Hydrogenation of C60 at 2 GPa Pressure and High Temperature. Chem. Phys. 325 (2006) 445-451
Howard J.A. EPR, FTIR, and FAB Mass Spectrometric Investigation of Reaction of H Atoms with C60 in a Cyclohexane Matrix. Chem. Phys. Lett. 203 (1993) 540-544
Brühweiler P.A., Anderson S., Dippel M., Mårtenson N., Demirev P.A., and Sundqvist U.R. Hydrogenation of Solid C60 by Atomic Hydrogen. Chem. Phys. Lett. 214 (1993) 45-49
Nossal J., Saini R.K., Alemany L.B., Meier M., and Billups W.E. The Synthesis and Characterization of Fullerene Hydrides. Eur. J. Org. Chem. 22 (2001) 4167-4180
Dorozhko P.A., Lobach A.S., Popov A.A., Senyavin V.M., and Korobov M.V. Sublimation of Hydrofullerenes C60H36 and C60H18. Chem. Phys. Lett. 336 (2001) 39-46
Wang N.X., and Zhang J.P. Preparation of C60H36. J. Phys. Chem. A 110 (2006) 6276-6278
Liang Z., and Marshall A.G. Precise Relative Ion Abundances from Fourier Transform Ion Cyclotron Resonance Magnitude-Mode Mass Spectra. Anal. Chem. 62 (1990) 70-75
Schneider N.S., Darwish A.D., Kroto H.W., Taylor R., and Walton D.R.M. Formation of Fullerols via Hydroboration of Fullerene-C60. J. Chem. Soc. Chem. Commun. 4 (1994) 463-464
Jusys Z., and Behm R.J. Methanol Oxidation on a Carbon-Supported Pt Fuel Cell Catalyst-A Kinetic and Mechanistic Study by Differential Electrochemical Mass Spectrometry. J. Phys. Chem. B 105 (2001) 10874-10883
Maiwald T., and Timmer J. Dynamical Modeling and Multi-Experiment Fitting with PottersWheel. Bioinformatics 24 (2008) 2037-2043
Tsang W. Energetics of Organic Free Radicals. In: Martinho Simoes J.A., Greenberg A., and Liebman J.F. (Eds). Heats of Formation of Organic Free Radicals by Kinetic Methods (1996), Blackie Academic and Professional, London 22-58
Bomse D.S., Woodin R.L., and Beauchamp J.L. Molecular Activation with Low-Intensity CW Infrared Laser Radiation. Multiphoton Dissociation of Ions Derived from Diethyl Ether. J. Am. Chem. Soc. 101 (1979) 5503-5512
Bettinger H.F., Rabuck A.D., Scuseria G.E., Wang N.X., Litosh V.A., Saini R.K., and Billups W.E. Pathways for the Thermally Induced Dehydrogenation of C60H2. Chem. Phys. Lett. 360 (2002) 509-514
Woodin R.L., Bomse D.S., and Beauchamp J.L. Multiphoton Dissociation of Molecules with Low Power Continuous Wave Infrared Laser Radiation. J. Am. Chem. Soc. 100 (1978) 3248-3250
Dunbar R.C. Kinetics of Low-Intensity Infrared Laser Photodissociation. The Thermal Model and Application of the Tolman Theorem. J. Chem. Phys. 95 (1991) 2537-2548
Haufler R.E., Wang L.S., Chibante L.P.F., Jin C., Conceicao J., Chai Y., and Smalley R.E. Fullerene Triplet State Production and Decay: R2PI Probes of C60 and C70 in a Supersonic Beam. Chem. Phys. Lett. 179 (1991) 449-454
Andersen J.U., Hvelplund P., Nielsen S.B., Pedersen U.V., and Tomita S. Statistical Electron Emission After Laser Excitation of C60-Ions from an Electrospray Source. Phys. Rev. A 65 (2002) 1-6
Billups W.E., Gonzalez A., Gesenberg C., Luo W., Marriott T., Alemany L.B., Saunders M., Jiménez-Vázquez H.A., and Khong A. 3He NMR Spectra of Highly Reduced C60. Tetrahedron Lett. 38 (1997) 175-178
Matsuzawa N., Fukunaga T., and Dixon D.A. Electronic Structures of 1,2- and 1,4-C60X2n Derivatives with n = 1, 2, 4, 6, 8, 10, 12, 18, 24, and 30. J. Phys. Chem. 96 (1992) 10747-10756