Reactions of gas-phase atomic metal ions with the macrocyclic ligand tribenzocyclotriyne

Dunbar, Robert C.; Uechi, Guy T.; Solooki, D.; Tessier, Claire A.; Youngs, Wiley J.; Asamoto, Bruce

doi:10.1021/ja00079a031

Cited by 32 publications

(33 citation statements)

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“…In the gas phase, K þ , Al þ , third-row transition metal ions Ti þ -Cu þ , Pb þ , and Ag þ reacted efficiently with vaporized tribenzocyclotriynes to form adducts that are stabilized by radiative cooling (Dunbar et al, 1991(Dunbar et al, , 1993. For Zn þ and Au þ , charge transfer dominates, and no complexes with the triyne ligand are formed.…”

Section: Host-guest Chemistry Of Calixarene and Resorcinarene Dementioning

confidence: 99%

Molecular recognition and supramolecular chemistry in the gas phase

Schalley

2001

Mass Spectrometry Reviews

289

178

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Supramolecular chemistry, in particular, the fields of molecular recognition and self-assembly, profit much from the development of soft ionization techniques and advanced methods for mass analysis and gas-phase chemistry. Vice versa, weakly bonded architectures and host-guest complexes represent a veritable challenge for the mass spectrometrist, leading to further development of methods and techniques. This review describes the state-of-the-art in this field, and includes topics such as the effects of solvation on meta binding to crown ethers, chiral discrimination of guests by chiral hosts, the elucidation of the secondary structure of self assembled complexes, and the mechanistic pathways of self assembly or the fragmentations of supramolecular complexes in the gas phase.

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Section: Host-guest Chemistry Of Calixarene and Resorcinarene Dementioning

confidence: 99%

Molecular recognition and supramolecular chemistry in the gas phase

Schalley

2001

Mass Spectrometry Reviews

289

178

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“…Other quantitative estimations of the relative reactivities for various metal ions were obtained by converting the rate constant for each 1 : 1 complexation into the corresponding reaction efficiency. 55,79 Large sets of low-energy CID experiments, where laser-desorbed alkali metal ionÈcrown ether complexes were dissociated in an FTICR mass spectrometer at different centre-of-mass kinetic energies were exploited to obtain the appearance energies for the dissociated metal ions.57 These values were corrected by the estimated internal energies of the complexes, yielding approximate evaluations of the absolute interaction energies between hosts and guests. For 18-crown-6 these interaction energies ranged from 134 to 167 kJ mol~1.…”

Section: Energeticsmentioning

confidence: 99%

Special feature: Perspective. Host–guest chemistry in the mass spectrometer

Vincenti

1995

J. Mass Spectrom.

122

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The study of host-guest chemistry in the gas phase has been pursued systematically only in the last 5 years, after sporadic interest in the 1980s, despite extensive investigation of this chemistry in the condensed phase and the success encountered in several Ðelds of application. Most gas-phase studies have been performed under the controlled conditions that can be achieved inside a mass spectrometer, where solvent e †ects are not present. At this point, the Ðrst evaluation of the achievements and knowledge emerging from these mass spectrometric investigations can be attempted. At the same time, it is possible to evaluate the most promising subjects for future research. This review undertakes these tasks, by presenting (i) applications where mass spectrometry was used to investigate condensed phase equilibria and, more extensively, (ii) experiments where host-guest complexes were formed directly in the gas phase. The latter processes are discussed in detail in relation to the structural and electronic e †ects, the energetic requirements and the dependence on size, rigidity, spatial geometry and functional groups of both hosts and guests. All these e †ects combined are likely to contribute to the strength and multiplicity of the non-covalent bonds that allow the complex to be formed. The macro(poly)cyclic hosts considered include crown ethers, cryptands, cyclodextrins, calixarenes, cryptophanes, cavitands, carcerands and macrolides. The guests are either metal cations or organic molecules and ions.

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“…18 It is an ongoing goal of our group to deepen the understanding of π/cation binding for larger, more complex π surfaces and for a variety of ionic species. 8,[19][20][21][22] The shape of the metal-ion/substrate binding energy surface is important in accurate theoretical modeling of dissociation reaction kinetics involving such complexes. The semiclassical variational transition state (VTST) approach worked out by Marcus, Wardlaw, Klippenstein, and co-workers [23][24][25] uses the classical phase space available to the "transitional" modes (the degrees of freedom with predominant metal character in this case) in both the dissociating complex and the transition state.…”

Section: Introductionmentioning

confidence: 99%

Binding of Na⁺, Mg⁺, and Al⁺ to the π Faces of Naphthalene and Indole: Ab Initio Mapping Study

Dunbar

1998

J. Phys. Chem. A

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Binding energy maps have been calculated for the binding of Na + , Mg + , and Al + to the entire π-facial region of indole and to the parts of the naphthalene face near the long central axis. Binding sites exist for all three cations over the phenyl ring and over the pyrrole ring of indole, although for Na + the pyrrole site almost disappears. The phenyl binding site of indole is in all cases about 4 kcal mol -1 more stable than the pyrrole site and about 6 kcal mol -1 more stable than the similar site in naphthalene. The Hartree-Fock calculations suggested an additional stable binding site for the open-shell Mg + ion over the nitrogen atom of indole, but this site was not reproduced by density-functional calculations and may well be a computational artifact. A differential electrostatic picture is considered in which the π face of indole is equivalent, in its cation interactions, to the π face of naphthalene, with the addition of a differential electrostatic field equal to the difference in the electrostatic fields surrounding naphthalene and indole. The differential electrostatic picture is highly successful for Na + , almost as successful for Al + , and almost as successful for Mg + . This gives quantitative support to the validity of an electrostatic approach to understanding, comparing, and predicting cation binding properties of different π-facial molecules.

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Reactions of gas-phase atomic metal ions with the macrocyclic ligand tribenzocyclotriyne

Cited by 32 publications

References 0 publications

Molecular recognition and supramolecular chemistry in the gas phase

Molecular recognition and supramolecular chemistry in the gas phase

Special feature: Perspective. Host–guest chemistry in the mass spectrometer

Binding of Na⁺, Mg⁺, and Al⁺ to the π Faces of Naphthalene and Indole: Ab Initio Mapping Study

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Reactions of gas-phase atomic metal ions with the macrocyclic ligand tribenzocyclotriyne

Cited by 32 publications

References 0 publications

Molecular recognition and supramolecular chemistry in the gas phase

Molecular recognition and supramolecular chemistry in the gas phase

Special feature: Perspective. Host–guest chemistry in the mass spectrometer

Binding of Na+, Mg+, and Al+ to the π Faces of Naphthalene and Indole: Ab Initio Mapping Study

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Binding of Na⁺, Mg⁺, and Al⁺ to the π Faces of Naphthalene and Indole: Ab Initio Mapping Study