A study of the electrospray ionisation of selected coumarin derivatives and their subsequent fragmentation using an ion trap mass spectrometer

Concannon, Shauna; Ramachandran, V. N.; Smyth, W. Franklin

doi:10.1002/1097-0231(20000730)14:14<1157::aid-rcm4>3.0.co;2-v

Cited by 50 publications

(55 citation statements)

References 12 publications

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“…Above 40 eV, m/z 203 is formed from B by carbon monoxide neutral loss whose intensity reaches more than 28% of the TIC for 5 and 6, whereas it is below 11% for 7. M/z 148 is formed by loss of iodo radical from m/z 275, and is seen only for 5, while iodo radical loss producing distonic radical cations m/z 104 and m/z 76, E and F, respectively, occurs for all three compounds, probably in the manner noted in the ESMS of iodo derivatives of coumarin [21]. The onset of formation of E and F are ϳ40 and 50 eV, respectively.…”

Section: Fragmentation Ofmentioning

confidence: 77%

Electrospray mass spectral fragmentation study of N,N′-disubstituted imidazolium ionic liquids

Lesimple

Mamer

Miao

et al. 2006

J. Am. Soc. Mass Spectrom.

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The tandem positive electrospray mass spectrometry (ESMS n ) fragmentation of ionic liquids incorporating the 1-methyl-imidazolium ring substituted on N II with an alkyl chain functionalized with an alcohol, carboxylic acid, or an iodobenzyl or iodobenzoyl ester is presented for the first time. The influence of chain length and function is studied. Esterified structures led to intense CID fragments lacking the imidazolium ring allowing full characterization of the ester moiety. Fragment ion compositions for this interesting and newly important class of compounds are established through accurate mass data and deuterium labeling. The presence of the cationic ring system produces intense even electron molecular cations in electrospray that undergo multiple stages of CID to yield fragments which often are radical cations. Unusual losses of methyl and hydrogen radicals are frequently noted. (J Am Soc Mass Spectrom 2006, 17, 85-95)

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Section: Fragmentation Ofmentioning

confidence: 77%

Electrospray mass spectral fragmentation study of N,N′-disubstituted imidazolium ionic liquids

Lesimple

Mamer

Miao

et al. 2006

J. Am. Soc. Mass Spectrom.

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“…MS 3 gives a signal at m/z 205.1 presumably corresponding to the loss of a methyl group from the methoxy group. Even though this is unlikely in this low-energy technique, such 15-u losses are observed for other methoxy-substituted aromatics such as coumarins [9,10]. MS 4 and MS 5 give rise to major signals at m/z 188.1 and 160.1, not observed using QTOFMS-MS.…”

Section: Narcotine (Iv)mentioning

confidence: 99%

Characterisation of selected drugs with nitrogen-containing saturated ring structures by use of electrospray ionisation with ion-trap mass spectrometry

et al. 2004

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The electrospray ionisation-ion-trap mass spectrometry (ESI-MS(n)) of selected drugs with nitrogen-containing saturated ring structures has been investigated. Sequential product-ion fragmentation experiments (MS(n)) have been performed to elucidate degradation pathways for the [M+H](+) ions and their predominant fragment ions. These MS(n) experiments result in characteristic fragmentations in which functional groups are generally cleaved from the ring systems as neutral molecules such as H(2)O, amines, alkenes, esters, carboxylic acids, etc. When such a nitrogen-containing drug molecule also contains a functional group, such as an ester, that on liberation as a neutral molecule has a significantly lower -Delta H(f) degrees value than that of the corresponding amine then the former is preferentially liberated. Furthermore, when an aromatic entity is present in these drug molecules together with the nitrogen-containing saturated ring structure fragmentation of the latter ring occurs with the former, predictably, being resistant to fragmentation. The structures of fragment ions proposed for ESI-MS(n) can be supported by electrospray ionisation-quadrupole time-of-flight mass spectrometry (ESI-QTOFMS). The data presented in this paper therefore provide useful information on the structure of these heterocyclic compounds which could be used to characterise unknown drug compounds isolated from natural sources, for example.

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“…To investigate the positions of the labeled oxygen atom, MS/MS fragmentation experiments of the protonated molecular ions of umbelliferone in the positive ion mode were performed. The fragments were assigned according to Concannon et al (2000). The ion at m/z 163 fragmented with the loss of CO and CO 2 to give a signal at m/z 135 and 119, respectively (Fig.…”

Section: Resultsmentioning

confidence: 81%

Biosynthetic Origin of the 1-Oxygen of Umbelliferone in the Root Tissue of Sweet Potato

Shimizu

Kai

Tamai

et al. 2008

Zeitschrift Für Naturforschung C

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A study of the electrospray ionisation of selected coumarin derivatives and their subsequent fragmentation using an ion trap mass spectrometer

Cited by 50 publications

References 12 publications

Electrospray mass spectral fragmentation study of N,N′-disubstituted imidazolium ionic liquids

Electrospray mass spectral fragmentation study of N,N′-disubstituted imidazolium ionic liquids

Characterisation of selected drugs with nitrogen-containing saturated ring structures by use of electrospray ionisation with ion-trap mass spectrometry

Biosynthetic Origin of the 1-Oxygen of Umbelliferone in the Root Tissue of Sweet Potato

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