Characterization of cardenolides by field ionization mass spectrometry

Brown, Peter; Brüschweiler, Fred; Pettit, George R.; Reichstein, T.

doi:10.1021/ja00717a063

Cited by 22 publications

(2 citation statements)

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“…Electron tunneling is well known in field ionization where electrons can tunnel a few angstroms from a molecule, through the potential barrier, to a suitably charged surface. Electric field strengths on the order of volts per angstrom are required for tunneling [83]. Similar phenomena also are observed in scanning tunneling microscopy [84].…”

Section: Local Electron Affinitiessupporting

confidence: 59%

Estimation of the electron affinities of C₆₀, corannulene, and coronene by using the kinetic method

Chen

Cooks

Corpuz

et al. 1996

J. Am. Soc. Mass Spectrom.

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Novel anions that contain one molecule each of C 60 and the polycyclic aromatic hydrocarbon coronene are generated in the gas phase by electron attachment desorption chemical ionization. Collision-induced dissociation reveals that these cluster ions are loosely bonded. Fragmentation of the mass-selected cluster anion yields, as the only products, the intact radical anions of the constituent molecules, namely, the C 60 radical anion and the coronene radical anion, in almost identical relative abundances. This result is interpreted as evidence that the cluster ion can be considered as the anion radical of one molecule solvated by the other molecule. The known very high electron affinity of C 60 (2.66 eV) and the comparable degree to which C 60 and the PAH compete for the electron suggests that dissociation may be controlled by the electron affinity of a portion of the C 60 surface, that is, in this case the kinetic method yields information on the "local" electron affinity of C 60 • The electron affinity of the bowl-shaped compound corannulene is estimated for the first time to be 0.50 ± 0.10 eV by the kinetic method by using a variety of reference compounds. Unlike coronene, corannulene reacts with C;.;t in the gas phase to form a covalently bonded, dehydrogenated cluster ion. Support for the concept of "local" electron affinity of C 60 comes from a theoretical calculation on the electronic structure of C 60 anions, which shows evidence for localization of the charge in the C 60 molecule. The possibility of electron tunneling in the C 60-coronene system is discussed as an alternative explanation for the unusual observation of equal abundances of C 60 anions and coronene anions upon dissociation of the corresponding cluster ion.

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Section: Local Electron Affinitiessupporting

confidence: 59%

Estimation of the electron affinities of C₆₀, corannulene, and coronene by using the kinetic method

Chen

Cooks

Corpuz

et al. 1996

J. Am. Soc. Mass Spectrom.

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“…For an analogous 5p(H),14a(H)-steroid without the 7a-OH, the resonance ofC(9) would be expected at ca. 43.5 ppm and the C(14) resonance at ca. 56.7 ppm.…”

Section: ~Ila-diucetoxy-8~14~-dihydroxy-i2-oxoetiunic-acid Methylementioning

confidence: 99%

Chemical Degradation of Sarverogenin, Proof for the Presence of the Steroid Carbon Skeleton. Glycosides and Aglycones, 335th Communication

Lardon

Reichsten

1987

Helvetica Chimica Acta

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Mass spectra of spirostanol and furostanol glycosides

Komori

Ida

Mutou

et al. 1975

Biol. Mass Spectrom.

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The electron impact mass spectra of twenty acetates and methylates of spirostanol and related furostanol glycosides of high molecular weight (above 650) have been investigated, and the most probable fragmentation patterns of the glycoside derivatives are presented. High resolution mass spectrometry provides useful information concerning the structures of both aglycone and sugar moieties as well as the molecular size of the oligoglycosides.

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Characterization of cardenolides by field ionization mass spectrometry

Cited by 22 publications

References 1 publication

Estimation of the electron affinities of C₆₀, corannulene, and coronene by using the kinetic method

Estimation of the electron affinities of C₆₀, corannulene, and coronene by using the kinetic method

Chemical Degradation of Sarverogenin, Proof for the Presence of the Steroid Carbon Skeleton. Glycosides and Aglycones, 335th Communication

Mass spectra of spirostanol and furostanol glycosides

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Characterization of cardenolides by field ionization mass spectrometry

Cited by 22 publications

References 1 publication

Estimation of the electron affinities of C60, corannulene, and coronene by using the kinetic method

Estimation of the electron affinities of C60, corannulene, and coronene by using the kinetic method

Chemical Degradation of Sarverogenin, Proof for the Presence of the Steroid Carbon Skeleton. Glycosides and Aglycones, 335th Communication

Mass spectra of spirostanol and furostanol glycosides

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Product

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Estimation of the electron affinities of C₆₀, corannulene, and coronene by using the kinetic method

Estimation of the electron affinities of C₆₀, corannulene, and coronene by using the kinetic method