Ion−Ion Collisions Leading to Formation of C−C Bonds at Surfaces:  An Interfacial Kolbe Reaction

Shen, Jie; Evans, Chris; Wade, and Nathan; Cooks, R. Graham

doi:10.1021/ja9906094

Cited by 31 publications

(48 citation statements)

References 22 publications

(14 reference statements)

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Section: G Analysis Of Modified Surfacesmentioning

confidence: 99%

“…25,203 Exact mass measurements taken by TOF-SIMS analysis have been used to confirm surface modification in several cases. 25,204,205 However, the most common method of characterizing the modified surfaces has been to use another form of hyperthermal energy collision-low energy chemical sputtering ͑vide infra͒. 54 In this experiment, Xe ϩ. , CF 3 ϩ or other ions are used to characterize the modified adsorbate by sputtering and associated charge exchange using low-energy projectile ions.…”

Section: G Analysis Of Modified Surfacesmentioning

confidence: 99%

See 1 more Smart Citation

Collisions of ions with surfaces at chemically relevant energies: Instrumentation and phenomena

Grill¹,

Shen²,

Evans³

et al. 2001

Review of Scientific Instruments

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201

249

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Articles you may be interested inMeasuring the internal energies of species emitted from hypervelocity nanoprojectile impacts on surfaces using recalibrated benzylpyridinium probe ions High-energy ions and atoms sputtered and reflected from a magnetron source for deposition of magnetic thin films J. Vac. Sci. Technol. A 23, 671 (2005); 10. 1116/1.1943452 Surface induced dissociations of protonated ethanol monomer, dimer and trimer ions: Trimer break-down graph from the collision energy dependence of projectile fragmentation An overview of gaseous ion/surface collisions is presented, with special emphasis on the behavior of polyatomic projectile ions at hyperthermal collision energies ͑1-100 eV͒ and the instrumentation needed for such studies. The inelastic and reactive processes occurring during ion/surface collisions are described in terms of several archetypes, viz., elastic and quasielastic scattering, chemical sputtering leading to release of surface material, inelastic scattering leading to surface-induced dissociation ͑SID͒ of the projectile, ion/surface reactions, and soft landing. Parameters that are important in ion/surface interactions are discussed, including the interaction time, the conversion of translational to internal energy, the translational energies of the scattered ions, the effects of scattering angle, and the influence of the nature of the surface. Different types of tandem mass spectrometers, built specifically to study ion/surface collision phenomena, are discussed and the advantages and disadvantages of the individual designs are compared. The role of SID as a technique in bioanalytical mass spectrometry is illustrated and this inelastic collision experiment is compared and contrasted with gas-phase collision-induced dissociation, the standard method of tandem mass spectrometry. Special emphasis is placed on reactive scattering including the use of ion/surface reactions for surface chemical analysis and for surface chemical modification.

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Section: G Analysis Of Modified Surfacesmentioning

confidence: 99%

Section: G Analysis Of Modified Surfacesmentioning

confidence: 99%

Collisions of ions with surfaces at chemically relevant energies: Instrumentation and phenomena

Grill¹,

Shen²,

Evans³

et al. 2001

Review of Scientific Instruments

Self Cite

201

249

View full text Add to dashboard Cite

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“…This early mass spectrometric study of ion/surface collisions is just one of many areas of mass spectrometry in which John Beynon made seminal contributions. Collisions of ions with surfaces in the hyperthermal collision energy range (<100 eV) represent a subject that has contributed to the elucidation of ion structure [2,3], the chemical analysis of surfaces [4,5], and the preparation of chemically modified surfaces [6,7]. Apart from these and other potential applications, attention has also been attracted to this area because of the variety and diversity of the processes involved, namely surface-induced dissociation (SID), ion/surface reactions, and chemical sputtering of surface molecules as gas-phase ions.…”

Section: Introductionmentioning

confidence: 99%

“…Covalent addition of polyatomic cations at functionalized organic surfaces has also been demonstrated. Aromatic ions, such as the (M − H) + ion of chlorobenzene [6] covalently binds to a carboxylic acid terminated self-assembled monolayer surface through an ion/surface decarboxylation reaction, which is reminiscent of the condensed phase Kolbe reaction. Furthermore, hydroxy-terminated SAMs have been transformed into terminal esters [32] and silyl ethers [33] through reactions with such cations as the benzoyl cation, C 6 H 5 CO + , and the trimethylsilyl cation, Si(CH 3 ) 3 + .…”

Section: Introductionmentioning

confidence: 99%

Differentiation of isomeric oxygenated adsorbates using low-energy ion/surface collisions

Wade

Gologan

et al. 2003

International Journal of Mass Spectrometry

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“…It also provides access to key properties and intrinsic reactivities of a great variety of solvent-and counterion-free gaseous ions and, as such, constitutes a powerful tool for chemical studies. Many classic organic reactions have been studied in the gas phase using the mass spectrometric methods [5][6][7][8][9][10][11][12][13][14]. Recently, with the advent of electrospray ionization (ESI) and atmospheric pressure chemical ionization (APCI), mass spectrometry has been widely used as an analytical tool for the study of atmospheric pressure ion/molecule reactions.…”

mentioning

confidence: 99%

Gas-phase Meerwein reaction of epoxides with protonated acetonitrile generated by atmospheric pressure ionizations

Liu

Kord

2010

J. Am. Soc. Mass Spectrom.

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Ethylnitrilium ion can be generated by protonation of acetonitrile (when used as the LC-MS mobile phase) under the conditions of atmospheric pressure ionizations, including electrospray ionization (ESI) and atmospheric pressure chemical ionization (APCI) as well as atmospheric pressure photoionization (APPI). Ethylnitrilium ion (CH 3 Ϫ C ϵ N ϩ H and its canonical form CH 3 Ϫ C ϩ ϭ NH) is shown to efficiently undergo the gas-phase Meerwein reaction with epoxides. This reaction proceeds by the initial formation of an oxonium ion followed by three-to-five-membered ring expansion via an intramolecular nucleophilic attack to yield the Meerwein reaction products. The density functional theory (DFT) calculations at the B3LYP/6-311ϩG(d,p) level show that the gas-phase Meerwein reaction is thermodynamically favorable. Collision-induced dissociation (CID) of the Meerwein reaction products yields the net oxygen-by-nitrogen replacement of epoxides with a characteristic mass shift of 1 Da, providing evidence for the cyclic nature of the gas-phase Meerwein reaction products. The gas-phase Meerwein reaction offers a novel and fast LC-MS approach for the direct analysis of epoxides that might be of genotoxic concern during drug development. Understanding and utilizing this unique gas-phase ion/molecule reaction, the sensitivity and selectivity for quantitation of epoxides can be enhanced. (J Am Soc Mass Spectrom 2010, 21, 1802-1813) © 2010 American Society for Mass Spectrometry G as-phase ion/molecule reactions are fast, efficient, and highly sensitive to the fine structural variations such as relative positions of functional groups. Their product distributions often provide diagnostic information for structural characterization of both reactant ions and neutral molecules [1][2][3][4]. Ion/ molecule reactions have also contributed significantly to the elucidation of organic reaction mechanisms, helping to bridge the gap between gas-phase ion chemistry and condensed-phase organic chemistry. It also provides access to key properties and intrinsic reactivities of a great variety of solvent-and counterion-free gaseous ions and, as such, constitutes a powerful tool for chemical studies. Many classic organic reactions have been studied in the gas phase using the mass spectrometric methods [5][6][7][8][9][10][11][12][13][14]. Recently, with the advent of electrospray ionization (ESI) and atmospheric pressure chemical ionization (APCI), mass spectrometry has been widely used as an analytical tool for the study of atmospheric pressure ion/molecule reactions. These gas-phase reactions can even yield detailed information regarding the individual reaction step of the catalytic cycles, and thus allow the study of transient intermediates that have not been accessible previously by the condensed-phase techniques [15,16].Epoxides are common reagents or key intermediates in a wide variety of synthetically important condensedphase reactions, including asymmetric synthesis via the opening of the oxirane ring [17][18][19]. For example, Meerwein fi...

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Ion−Ion Collisions Leading to Formation of C−C Bonds at Surfaces: An Interfacial Kolbe Reaction

Cited by 31 publications

References 22 publications

Collisions of ions with surfaces at chemically relevant energies: Instrumentation and phenomena

Collisions of ions with surfaces at chemically relevant energies: Instrumentation and phenomena

Differentiation of isomeric oxygenated adsorbates using low-energy ion/surface collisions

Gas-phase Meerwein reaction of epoxides with protonated acetonitrile generated by atmospheric pressure ionizations

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