Understanding Nontraditional Differential Mobility Behavior: A Case Study of the Tricarbastannatrane Cation, N(CH2CH2CH2)3Sn+

Crouse, Jeff; Haack, Alexander; Benter, Thorsten; Hopkins, W. Scott

doi:10.1021/jasms.9b00042

Cited by 15 publications

(28 citation statements)

References 41 publications

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“…The temperature dependence of the Type B feature is more interesting. As the gas temperature is increased to T = 300 °C, the dispersion curve evolves from Type B to Type C to the exotic Type D behavior, wherein at high SV values, the optimal CV reaches a maximum and then begins to decrease. , Type D behavior is generally attributed to strongly bound ion–solvent clusters, in this case [M + H + MeCN] + , which undergo field-induced dissociation at high SV values and adopt Type A behavior as the bare ion.…”

Section: Resultsmentioning

confidence: 99%

UVPD Spectroscopy of Differential Mobility-Selected Prototropic Isomers of Rivaroxaban

et al. 2021

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Two ion populations of protonated Rivaroxaban, [C 19 H 18 ClN 3 O 5 S + H] + , are separated under pure N 2 conditions using differential mobility spectrometry prior to characterization in a hybrid triple quadrupole linear ion trap mass spectrometer. These populations are attributed to bare protonated Rivaroxaban and to a proton-bound Rivaroxaban−ammonia complex, which dissociates prior to mass-selecting the parent ion. Ultraviolet photodissociation (UVPD) and collision-induced dissociation (CID) studies indicate that both protonated Rivaroxaban ion populations are comprised of the computed global minimum prototropic isomer. Two ion populations are also observed when the collision environment is modified with 1.5% (v/v) acetonitrile. In this case, the protonated Rivaroxaban ion populations are produced by the dissociation of the ammonium complex and by the dissociation of a proton-bound Rivaroxaban−acetonitrile complex prior to mass selection. Again, both populations exhibit a similar CID behavior; however, UVPD spectra indicate that the two ion populations are associated with different prototropic isomers. The experimentally acquired spectra are compared with computed spectra and are assigned to two prototropic isomers that exhibit proton sharing between distal oxygen centers.

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Section: Resultsmentioning

confidence: 99%

UVPD Spectroscopy of Differential Mobility-Selected Prototropic Isomers of Rivaroxaban

et al. 2021

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“…Further evidence to support protonation induced chirality as the separation mechanism can be ascertained by modelling the DMS behaviour of Verapamil and Norverapamil. [45,46] The modelling protocol employs firstprinciples IMS theory, [47] which incorporates the temperature-dependent CCS of each conformation present in the gas-phase ensemble. A comparison of the experimental and simulated dispersion curves (i.e., a plot of the CV required for ion elution as a function of SV) for N-protonated Verapamil and Norverapamil is shown in Figures S5 and S6, respectively.…”

Section: Methodsmentioning

confidence: 99%

“…Further evidence to support protonation induced chirality as the separation mechanism can be ascertained by modelling the DMS behaviour of Verapamil and Norverapamil [45, 46] . The modelling protocol employs first‐principles IMS theory, [47] which incorporates the temperature‐dependent CCS of each conformation present in the gas‐phase ensemble.…”

Section: Figurementioning

confidence: 99%

Protonation‐Induced Chirality Drives Separation by Differential Ion Mobility Spectrometry

Ieritano

Blanc²,

Schneider³

et al. 2022

Angew Chem Int Ed

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Upon development of a workflow to analyze (�)-Verapamil and its metabolites using differential mobility spectrometry (DMS), we noticed that the ionogram of protonated Verapamil consisted of two peaks. This was inconsistent with its metabolites, as each exhibited only a single peak in the respective ionograms. The unique behaviour of Verapamil was attributed to protonation at its tertiary amino moiety, which generated a stereogenic quaternary amine. The introduction of additional chirality upon Nprotonation of Verapamil renders four possible stereochemical configurations for the protonated ion:

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Section: Figurementioning

confidence: 99%

Protonation‐Induced Chirality Drives Separation by Differential Ion Mobility Spectrometry

Ieritano

Blanc²,

Schneider³

et al. 2022

Angewandte Chemie

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View full text Add to dashboard Cite

Upon development of a workflow to analyze (±)‐Verapamil and its metabolites using differential mobility spectrometry (DMS), we noticed that the ionogram of protonated Verapamil consisted of two peaks. This was inconsistent with its metabolites, as each exhibited only a single peak in the respective ionograms. The unique behaviour of Verapamil was attributed to protonation at its tertiary amino moiety, which generated a stereogenic quaternary amine. The introduction of additional chirality upon N‐protonation of Verapamil renders four possible stereochemical configurations for the protonated ion: (R,R), (S,S), (R,S), or (S,R). The (R,R)/(S,S) and (R,S)/(S,R) enantiomeric pairs are diastereomeric and thus exhibit unique conformations that are resolvable by linear and differential ion mobility techniques. Protonation‐induced chirality appears to be a general phenomenon, as N‐protonation of 12 additional chiral amines generated diastereomers that were readily resolved by DMS.

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Understanding Nontraditional Differential Mobility Behavior: A Case Study of the Tricarbastannatrane Cation, N(CH₂CH₂CH₂)₃Sn⁺

Cited by 15 publications

References 41 publications

UVPD Spectroscopy of Differential Mobility-Selected Prototropic Isomers of Rivaroxaban

UVPD Spectroscopy of Differential Mobility-Selected Prototropic Isomers of Rivaroxaban

Protonation‐Induced Chirality Drives Separation by Differential Ion Mobility Spectrometry

Protonation‐Induced Chirality Drives Separation by Differential Ion Mobility Spectrometry

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