The ion–molecule reactions of the rhenium oxide anions, [ReOx]− (x = 2–4) with the organic substrates methane, ethene, methanol, and acetic acid have been examined in a linear ion trap mass spectrometer. The only reactivity observed was between [ReO2]− and acetic acid. Isotope-labelled experiments and high-resolution mass spectrometry measurements were used to assign the formulas of the ionic products. Collision-induced dissociation and ion–molecule reactions with acetic acid were used to probe the structures of the mass-selected primary product ions. Density functional theory calculations [PBE0/LanL2DZ6-311+G(d)] were used to suggest possible structures. The three primary product channels observed are likely to arise from the formation of the metallalactone [ReO2(CH2CO2)]− (m/z 277) and H2, [CH3ReO2(OH)]− (m/z 251) and CO, and [ReO3]− (m/z 235), H2 and CH2CO.
SchwarzH., “How and why do cluster size, charge state, and ligands affect the course of metal-mediated gas-phase activation of methane?”, Isr. J. Chem.54, 1413 (2014). doi: http://dx.doi.org/10.1002/ijch.201300134
8.
BellR.C.ZemskiK.A.KernsK.P.DengH.T.CastlemanA.W., “Gas-phase chemistry of vanadium oxide cluster cations. 1. Reactions with C2F6 and CH3CF3”, J. Phys. Chem. A102, 1733 (1998). doi: http://dx.doi.org/10.1021/jp9734538
9.
BellR.C.CastlemanA.W., “Reactions of vanadium oxide cluster ions with 1,3-butadiene and isomers of butene”, J. Phys. Chem. A106, 9893 (2002). doi: http://dx.doi.org/10.1021/jp020559g
10.
JustesD.R.MitricR.MooreN.A.Bonacic-KouteckyV.CastlemanA.W., “Theoretical and experimental consideration of the reactions between VxOy+ and ethylene”, J. Am. Chem. Soc.125, 6289 (2003). doi: http://dx.doi.org/10.1021/ja021349k
11.
MooreN.A.MitricR.JustesD.R.Bonacic-KouteckyV.CastlemanA.W., “Kinetic analysis of the reaction between (V2O5)n=1,2+ and ethylene”, J. Phys. Chem. B110, 3015 (2006). doi: http://dx.doi.org/10.1021/jp055652u
12.
JustesD.R.MooreN.A.CastlemanA.W., “Reactions of vanadium and niobium oxides with methanol”, J. Phys. Chem. B108, 3855 (2004). doi: http://dx.doi.org/10.1021/jp031152u
EngeserM.SchröderD.SchwarzH., “Gas-phase dehydrogenation of methanol with mononuclear vanadium-oxide cations”, Chem. Eur. J.11, 5975 (2005). doi: http://dx.doi.org/10.1002/chem.200401352
15.
FialkoE.F.KikhtenkoA.V.GoncharovV.B.ZamaraevK.I., “Similarities between reactions of methanol with MoxOy+ in the gas phase and over real catalysts”, J. Phys. Chem. B101, 5772 (1997). doi: http://dx.doi.org/10.1021/jp963848b
16.
FialkoE.F.KikhtenkoA.V.GoncharovV.B., “Molybdenum oxide cluster ions in the gas phase: Reactions with small alcohols”, Organometallics17, 25 (1998). doi: http://dx.doi.org/10.1021/om9704253
17.
OliveiraM.C.MarçaloJ.VieiraM.C.FerreiraacM.A. Almoster, “Formation of some transition metal oxide cluster anions and reactivity towards methanol in the gas phase”, Int. J. Mass Spectrom.187, 825 (1999). doi: http://dx.doi.org/10.1016/S1387-3806(98)14199-4
18.
WatersT.O'HairR.A.J.WeddA.G., “Probing the catalytic oxidation of alcohols via an anionic dimolybdate centre using multistage mass spectrometry”, Chem. Comm.3, 225 (2000). doi: http://dx.doi.org/10.1039/a909353b
19.
WatersT.O'HairR.A.J.WeddA.G., “Catalytic gas phase oxidation of methanol to formaldehyde”, J. Am. Chem. Soc.125, 3384 (2003). doi: http://dx.doi.org/10.1021/ja028839x
WatersT.KhairallahG.N.WimalaS.A.S.Y.AngY.C.O'HairR.A.J.WeddA.G., “Mononuclear metavanadate catalyses gas phase oxidation of methanol to formaldehyde employing dioxygen as the terminal oxidant”, Chem. Comm.43, 4503 (2006). doi: http://dx.doi.org/10.1039/b612384h
22.
WatersT.WeddA.G.O'HairR.A.J., “Gas-phase reactivity of metavanadate [VO3]− towards methanol and ethanol: Experiment and theory”, Chem. Eur. J.13, 8818 (2007). doi: http://dx.doi.org/10.1002/chem.200700619
23.
HarrisB.L.WatersT.KhairallahG.N.O'HairR.A.J., “Gas phase reactions of [VO2(OH)2]− and [V2O5(OH)]− with methanol: Experiment and theory”, J. Phys. Chem. A117, 1124 (2013). doi: http://dx.doi.org/10.1021/jp3046142
24.
BurnierR.C.ByrdG.D.FreiserB.S., “Copper(i) chemical ionization–mass spectrometric analysis of esters and ketones”, Anal. Chem.52, 1641 (1980). doi: http://dx.doi.org/10.1021/ac50061a026
25.
LombarskiM.AllisonJ., “Metal ion chemical ionization. Part II. The gas phase chemistry of Co+ with thiols, butanone, 3-butenone, carboxylic acids, substituted butanones, and substituted carboxylic acids”, Int. J. Mass Spectrom. Ion Proc.65, 31 (1985). doi: http://dx.doi.org/10.1016/0168-1176(85)85052-7
26.
SchroederD.ZummackW.SchwarzH., “Reaction products, directionalities, and mechanisms of iron(i)-mediated CH-, CC-, and CO-bond activation of aliphatic carboxylic acids in the gas phase”, J. Am. Chem. Soc.116, 5857 (1994). doi: http://dx.doi.org/10.1021/ja00092a041
O'HairR.A.J.VrkicA.K.JamesP.F., “Gas phase synthesis and reactivity of the organomagnesates [CH3MgL2]− (L = Cl and = O2CCH3): From ligand effects to catalysis”, J. Am. Chem. Soc.126, 12173 (2004). doi: http://dx.doi.org/10.1021/ja048476w
29.
WoolleyM.J.KhairallahG.N.da SilvaG.R.DonnellyP.S.O'HairR.A.J., “Direct versus water-mediated protodecarboxylation of acetic acid catalyzed by group 10 carboxylates, [(phen)M(O2CCH3)]+”, Organometallics33, 5185 (2014). doi: http://dx.doi.org/10.1021/om500493w
30.
WatersT.O'HairR.A.J., in The Encyclopedia of Mass Spectrometry Volume 4: Fundamentals of and applications to organic (and organometallic) compounds, Ed by GrossM.L.CaprioliR.M.NibberingN.M.M.). Elsevier, Amsterdam, p. 604 (2005).
31.
BöhmeD.K.SchwarzH., “Gas-phase catalysis by atomic and cluster metal ions: The ultimate single-site catalysts”, Angew. Chem. Int. Ed.44, 2336 (2005). doi: http://dx.doi.org/10.1002/anie.200461698
32.
O'HairR.A.J., “Mass spectrometry based studies of gas phase metal catalyzed reactions”, Int. J. Mass Spectrom.377, 121 (2015). doi: http://dx.doi.org/10.1016/j.ijms.2014.05.003
33.
RomaoC.C.KuhnF.E.HerrmannW.A., “Rhenium(vii) oxo and imido complexes: Synthesis, structures, and applications”, Chem. Rev.97, 3197 (1997). doi: http://dx.doi.org/10.1021/cr9703212
KorstanjeT.J.GebbinkR.J.M.K., “Catalytic oxidation and deoxygenation of renewables with rhenium complexes”. Top. Organomet. Chem.39, 129 (2012). doi: http://dx.doi.org/10.1007/978-3-642-28288-1_4
36.
CanaleV.TonucciL.BressanM.d'AlessandroN., “Deoxydehydration of glycerol to allyl alcohol catalyzed by rhenium derivatives”, Catal. Sci. Technol.4, 3697 (2014). doi: http://dx.doi.org/10.1039/C4CY00631C
37.
FialkoE.A.KikhtenkoA.V.GoncharovV.B.ZamaraevK.I., “Ion cyclotron resonance study of CO oxidation in the gas phase in the presence of rhenium cations with carbonyl and oxygen ligands. Comparison with heterogeneous catalysis”, Catal. Lett.41, 7 (1996). doi: http://dx.doi.org/10.1007/BF00811704
38.
BeyerM.K.BergC.B.BondybeyV.E., “Gas-phase reactions of rhenium–oxo species ReOnn = 0, 2–6, 8, with O2, N2O, CO, H2O, H2, CH4 and C2H4”, Phys. Chem. Chem. Phys.3, 1840 (2001). doi: http://dx.doi.org/10.1039/b100538n
39.
ChenX.ZhangX.ChenP., “Metallaoxetanes and carbenes from diolates in high-valent rhenium oxo chemistry: The importance of the coordination number”, Angew. Chem. Int. Ed.42, 3798 (2003). doi: http://dx.doi.org/10.1002/anie.200351496
40.
ZhangX.ChenX.ChenP., “Mass spectrometric study of the conversion of rhenium diolates to metallaoxetanes and carbenes. Coordination number, polar, and steric effects”, Organometallics23, 3437 (2004). doi: http://dx.doi.org/10.1021/om049737d
41.
NarancicS.ChenP., “Computational study of low-coordinate rhenium diolates, metallaoxetanes, oxo complexes, and carbenes”, Organometallics24, 10 (2005). doi: http://dx.doi.org/10.1021/om0491241
42.
ZhangX.NarancicS.ChenP., “Experimental and computational study of the [2 + 2] dissociation of rhenaoxetanes in the gas phase”, Organometallics24, 3040 (2005). doi: http://dx.doi.org/10.1021/om0502842
43.
LaiY.-Y.BornandM.ChenP., “Homogeneous model complexes for supported rhenia metathesis catalysts”, Organometallics, 31, 7558 (2012). doi: http://dx.doi.org/10.1021/om300852s
ChenW.J.ZhaiH.J.HuangX.WangL.S., “On the electronic structure of mono-rhenium oxide clusters: ReOn− and ReOn (n = 3, 4)”, Chem. Phys. Lett.512, 49 (2011). doi: http://dx.doi.org/10.1016/j.cplett.2011.07.018
46.
ZhouM.CitraA.LiangB.AndrewsL., “Infrared spectra and density functional calculations of MO2, MO3, (O2)MO2, MO4, MO2− (M = Re, Ru, Os) and ReO3−, ReO4− in solid neon and argon”, J. Phys. Chem. A, 104, 3457 (2000). doi: http://dx.doi.org/10.1021/jp993026p
47.
SahurekaF.BurnsR.C.Von Nagy-FelsobukiE.I., “Electrospray characterization of perrhenate systems”, J. Am. Soc. Mass Spectrom.12, 1136 (2001). doi: http://dx.doi.org/10.1016/S1044-0305(01)00298-7
48.
CenterR.E., “Ion-molecule experiments involving negative ions of tungsten and rhenium oxides”, J. Chem. Phys.56, 371 (1972). doi: http://dx.doi.org/10.1063/1.1676875
49.
O'HairR.A.J., “The 3D quadrupole ion trap mass spectrometer as a complete chemical laboratory for fundamental gas phase studies of metal mediated chemistry”, Chem. Commun.1469 (2006). doi: http://dx.doi.org/10.1039/b516348j
50.
O'HairR.A.J.RijsN.J., “Gas phase studies of the Pesci decarboxylation reaction: Synthesis, structure, and unimolecular and bimolecular reactivity of organometallic ions”, Acc. Chem. Res.48, 329 (2015). doi: http://dx.doi.org/10.1021/ar500377u
51.
FeketeováL.KhairallahG.N.O'HairR.A.J., “Intercluster chemistry of protonated and sodiated betaine dimers upon collision induced dissociation and electron induced dissociation”, Eur. J. Mass Spectrom.14, 107 (2008). doi: http://dx.doi.org/10.1255/ejms.911
52.
DonaldW.A.McKenzieC.J.O'HairR.A.J., “C–H bond activation of methanol and ethanol by a highspin FeIVO biomimetic complex”, Angew. Chem. Int. Ed.50, 8379 (2011). doi: http://dx.doi.org/10.1002/anie.201102146
53.
LamA.K.Y.LiC.KhairallahG.N.KirkB.B.BlanksbyS.J.TrevittA.J.WilleU.O'HairR.A.J.da SilvaG., “Gas-phase reactions of aryl radicals with 2-butyne: An experimental and theoretical investigation employing the N-methyl-pyridinium-4-yl radical cation”, Phys. Chem. Chem. Phys.14, 2417 (2012). doi: http://dx.doi.org/10.1039/c2cp22970f
54.
DonaldW.A.KhairallahG.N.O'HairR.A.J., “The effective temperature of ions stored in a linear quadrupole ion trap mass spectrometer”, J. Am. Soc. Mass Spectrom.24, 811 (2013). doi: http://dx.doi.org/10.1007/s13361-013-0625-x
55.
KuzmicP., “Program DYNAFIT for the analysis of enzyme kinetic data: Application to HIV proteinase”, Anal. Biochem.237, 260 (1996). doi: http://dx.doi.org/10.1006/abio.1996.0238
SunY.ChenH., “Performance of density functionals for activation energies of re-catalyzed organic reactions”, J. Chem. Theory Comput.10, 579 (2014). doi: http://dx.doi.org/10.1021/ct4010855
58.
HuberS.PöthigA.HerrmannW.A.KühnF.E., “Evaluation of theoretical functionals for structural and vibrational energy predictions on organo-rhenium (vii) oxides”, J. Organomet. Chem.760, 156 (2014). doi: http://dx.doi.org/10.1016/j.jorganchem.2013.11.008
59.
GancheffJ.S.DenisP.A.HahnF. Ekkehardt, “Assessment of density functional methods for the study of vanadium and rhenium complexes with thiolato ligands”, J. Mol. Struct. (Theochem)941, 1 (2010). doi: http://dx.doi.org/10.1016/j.theochem.2009.10.020
60.
DemoinD.W.LiY.JurissonS.S.DeakynC.A., “Method and basis set analysis of oxorhenium(v) complexes for theoretical calculations”, Comput. Theor. Chem.997, 34 (2012). doi: http://dx.doi.org/10.1016/j.comptc.2012.07.039
61.
AdamoC.BaroneV., “Toward reliable density functional methods without adjustable parameters: The PBE0 model”, J. Chem. Phys.110, 6158 (1999). doi: http://dx.doi.org/10.1063/1.478522
62.
HayP.J.WadtW.R., “Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals”, J. Chem. Phys.82, 299 (1985). doi: http://dx.doi.org/10.1063/1.448975
63.
KrishnanR.BinkleyJ.S.SeegerR.PopleJ.A., “Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions”, J. Chem. Phys.72, 650 (1980). doi: http://dx.doi.org/10.1063/1.438955
64.
FrischM.J.PopleJ.A.BinkleyJ.S., “Self-consistent molecular orbital methods. 25. Supplementary functions for Gaussian basis sets”, J. Chem. Phys.80, 3265 (1984). doi: http://dx.doi.org/10.1063/1.447079
65.
FranclM.M.PietroW. J.HehreW.J.BinkleyJ.S.GordonM.S.DeFreesD.J.PopleJ.A., “Self-consistent molecular orbital methods. XXIII. A polarization-type basis set for second-row elements”, J. Chem. Phys.77, 3654 (1982). doi: http://dx.doi.org/10.1063/1.444267
66.
AniagyeiA.TiaR.AdeiE., “A density functional theory study of the mechanisms of oxidation of ethylene by rhenium oxide complexes”, Dalton Trans.42, 10885 (2013). doi: http://dx.doi.org/10.1039/c3dt50539a
67.
VikseK.L.KhairallahG.N.O'HairR.A.J., “Gasphase unimolecular reactions of pallada- and nickelalactones”, Organometallics, 31, 7467 (2012). doi: http://dx.doi.org/10.1021/om300741n
68.
LaneK.R.SquiresR.R., “Formation of HCr(CO)3− from the remarkable reaction of hydride ion with benzenechromium tricarbonyl. Gas-phase reactions of a novel 14-electron metal anion complex”, J. Am. Chem. Soc.107, 6403 (1985). doi: http://dx.doi.org/10.1021/ja00308a048
69.
SuT.BowersM.T., “Ion-polar molecule collisions: The effect of ion size on ion–polar molecule rate constants; the parameterization of the average-dipole-orientation theory”, Int. J. Mass Spectrom. Ion Phys.12, 347 (1973). doi: http://dx.doi.org/10.1016/0020-7381(73)80104-4
70.
LimK.A., “COLRATE. QCPE 643: Calculation of gas-kinetic collision rate coefficients”, Quantum Chem. Program Exch.14, 1 (1994).
71.
SchroederD.ShaikS.SchwarzH., “Two-state reactivity as a new concept in organometallic chemistry”, Acc. Chem. Res.33, 139 (2000). doi: http://dx.doi.org/10.1021/ar990028j
72.
SchwarzH., “On the spin-forbiddeness of gas-phase ion–molecule reactions: A fruitful intersection of experimental and computational studies”, Int. J. Mass Spectrom.237, 75 (2004). doi: http://dx.doi.org/10.1016/j.ijms.2004.06.006
