Unravelling seemingly complex chemistry of reactions using electrospray ionization mass spectrometry

Bakhtiar, Ray; Hop, Cornelis E. C. A.

doi:10.1002/(sici)1099-1395(199907)12:7<511::aid-poc160>3.0.co;2-s

Cited by 24 publications

(15 citation statements)

References 280 publications

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“…4,21 Therefore, in order to overcome thermodynamic barriers and at the same time maintain the structural integrity of the analyte ions, a 'gentle' introduction of energy to achieve desolvation is required. This is accomplished via several approaches, depending on the instrumental design, with each having distinct advantages and drawbacks (vide infra).…”

Section: Electrospray Ionizationmentioning

confidence: 91%

“…MS methods of analysis are particularly attractive in investigations involving molecular recognition processes. [1][2][3][4] Results of these studies can be used in the design and development of novel analytical methods and to enhance our fundamental understanding of molecular interactions. An example of the application of molecular recognition in analytical chemistry is enantioselective chromatography.…”

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confidence: 96%

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Use of atmospheric pressure ionization mass spectrometry in enantioselective liquid chromatography

2001

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Recent advances in mass spectrometry have rendered it an attractive and versatile tool in industrial and academic research laboratories. As a part of this rapid growth, a considerable body of literature has been devoted to the application of mass spectrometry in studies involving enantioselectivity, molecular recognition, and supramolecular chemistry. In concert with separation techniques such as capillary electrophoresis and liquid chromatography, mass spectrometry allows rapid characterization of a large array of molecules in complex mixtures. A majority of these findings have been made possible by the introduction of 'soft-ionization' techniques such as electrospray ionization interface. Other techniques such as atmospheric pressure chemical ionization mass spectrometry have been widely used as a rugged interface for quantitative liquid chromatography-mass spectrometry. Herein, we present a brief overview of the above techniques accompanied with several examples of enantioselective capillary electrophoresis- and liquid chromatography-mass spectrometry in drug discovery and development. Although the emphasis of this article is on quantitative enantiomeric chromatography-mass spectrometry, we envisage that similar strategies are adaptable in qualitative studies.

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Section: Electrospray Ionizationmentioning

confidence: 91%

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confidence: 96%

Use of atmospheric pressure ionization mass spectrometry in enantioselective liquid chromatography

2001

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“…All experiments were conducted using a Micromass Quattro LC (Micromass, Manchester, England) equipped with an atmospheric chemical ionization (APCI) interface 6–10. The data system consisted of Masslynx Ver.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Crystal Structure of IM‐6, a New Open Framework Cobalt–Gallium Phosphate with Ten‐ and Twelve‐Membered Pore Openings

Josien

Simon‐Masseron

Gramlich³

et al. 2003

Chemistry A European J

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A new three-dimensional microporous cobalt-gallium phosphate, named IM-6, has been synthesized under solvothermal conditions with an N-substituted piperazine as organic template. The structure was solved by single-crystal X-ray diffraction (triclinic, P(-)1, a=9.848(20), b=12.470(32), c=12.603(28)A, alpha=63.47(16) degrees, beta=74.56(16) degrees, gamma=76.03(17) degrees). IM-6 exhibits a new framework topology. The inorganic framework is built up of MO(4) (M=Co, Ga) and PO(4) tetrahedra. It displays a two-dimensional interconnected channel system running along the [0(-)11] and [100] directions and delimited by ten- and twelve-membered ring openings, respectively.

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“…On the other hand, in the last two decades, the mass spectrometry capabilities have been dramatically extended by the development of laser desorption ionization and electrospray ionization (ESI) permitting to ionize nonvolatile molecules . Since its discovery, electrospray ionization mass spectrometry (ESI/MS) has emerged as a powerful tool in probing structural modifications of large molecules and to provide valuable information on structurally specific biomolecular interactions . However, the first reported uses of the ESI/MS technique for the detection of neutral organic molecules, including fullerenes, indicate that necessarily the analytes have to be derivatized either using specific tagging reagents or using their redox properties .…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2011

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The mass spectra of new substituted pyrrolidino[60]- and [70]fullerenes have been obtained using electrospray ionization conditions in the positive and negative mode of detection with two different mass spectrometers, a quadrupole ion trap and a Fourier transform ion cyclotron resonance. Radical anions M(●-) and deprotonated molecules [M-H](-) are formed under negative electrospray ionization mass spectrometry conditions, and the collision-induced dissociations of both ionic species have been studied. Either negative odd-electron ions or negative even-electron ions undergo a retro-cycloaddition process forming the corresponding fullerene product ions C(60)(●-) and C(70)(●-). The generation of fullerene radical anions from deprotonated molecules is a new exception of the "even-electron rule." In contrast, the protonated molecules [M + H](+) obtained from the positive mode of detection do not undergo this cycloreversion reaction, and the MS(n) experiment reveals a variety of eliminations of neutral molecules involving different hydrogen shifts and multiple bond cleavages that lead eventually to substituted methanofullerene fragment ions. The observed fragmentations can be correlated with the electronic character of the substituents attached to the heterocyclic moiety. The results obtained from the thermal reactions of these compounds, carried out under different pH conditions, correlate well with those obtained in gas phase. The different behaviors between protonated and unprotonated molecules and ions can be explained assuming that the retro-cycloaddition reaction takes place only when the nitrogen atom of the pyrrolidine ring (the basic center of the molecule) is unprotonated both in gas and condensed phase. The protonation of the NH group inhibits the cycloreversion process, and therefore different fragmentations take place. The detailed mechanisms of the formation and evolution of the intermediate fragments are described.

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Unravelling seemingly complex chemistry of reactions using electrospray ionization mass spectrometry

Cited by 24 publications

References 280 publications

Use of atmospheric pressure ionization mass spectrometry in enantioselective liquid chromatography

Use of atmospheric pressure ionization mass spectrometry in enantioselective liquid chromatography

Synthesis and Crystal Structure of IM‐6, a New Open Framework Cobalt–Gallium Phosphate with Ten‐ and Twelve‐Membered Pore Openings

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

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