Energy decomposition analysis of the interactions in adduct ions of acetophenone and Na+, NH4+ and H+ in the gas phase

Sugimura, Natsuhiko; Igarashi, Yoko; Aoyama, Reiko; Shibue, Toshimichi

doi:10.1016/j.cplett.2017.06.029

Cited by 3 publications

(7 citation statements)

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“…m/z 231 was base peak ion for 2 and 4 ). It is noteworthy to consider that the relative abundance of the ions might depend not only on the complex interaction energies but also on the cation concentration in solution and adducts fragmentation behavior in the ionization source …”

Section: Resultsmentioning

confidence: 99%

“…Computational models have been used to investigate the physicochemical interactions of Na + with organic compounds, as well as their influence on the compounds fragmentation . So to better understand the interactions and affinity of Na + with hirsutinolide and glaucolide SL, additional computational calculations study were performed using piptocarphin A ( 1 , hirsutinolide) and glaucolide A ( 2 , glaucolide), which were optimized for their geometry with the level of theory described in computational methodology section.…”

Section: Resultsmentioning

confidence: 99%

“…The sodium complexes interactions for the two evaluated compounds ( 1a1–2a4 ) occurred mainly in C‐13 acetoxy group and/or in carbonyl oxygen of γ‐butyrolactone ring (as previously observed in the atomistic molecular dynamics simulations), showing once more that it is the region of the structure with the highest oxygen chelation. One of the most significant properties in the ionization efficiency of oxygen bases for the Na + adducts formation is related to the chelating capacity of these bases, which indicates an electrostatic interaction in the sodium adducted ion …”

Section: Resultsmentioning

confidence: 99%

“…Therefore, tandem mass structure characterization assisted by computational physical‐chemical studies can support the proposed fragmentation and provide better understanding of molecular behavior in LC‐MS/MS analyses such as ionization and adducts formation …”

Section: Introductionmentioning

confidence: 97%

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ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na⁺/H⁺ adducts interactions in complex mixture

et al. 2019

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Sesquiterpene lactones (SL) have been reported with various biological effects.Among the described SL skeletons, hirsutinolide and glaucolide have not been extensively studied by mass spectrometry (MS), especially how to distinguish them in organic matrices. Thus, this paper reports (1) a strategy of their differentiation based on MS behavior during the ionization and (2) a proposal of the fragmentation pattern for both SL-subtypes. ESI(+)-HRMS data of four isolated SL (hirsutinolides 1 and 3; glaucolides 2 and 4) were recorded by direct and UPLC water-sample combined injections. These analyses revealed that hirsutinolides and glaucolides formed [M+Na] + ion during the operation of the direct MS injection, and ([M+Na] + and [M+H-H 2 O] + ) and[M+H] + ions were respectively observed for hirsutinolides and glaucolides during the operation of combined UPLC water and sample MS injection. Computational simulations showed that the complex hirsutinolide (1)-Na + formed with a lower preparation energy compared with the complex glaucolide (2)-Na + . However, despite their different behavior during the ionization process, ESI(+)-HRMS/MS analyses of 1-4 gave similar fragmentation patterns at m/z 277, 259, 241, and 231 that can be used as diagnostic ions for both skeletons. Moreover, the differentiation strategy based on the nature of the complex SL-adducts and their MS/MS fragmentation pattern were successfully applied for the chemical characterization of the extract from Vernonanthura tweedieana using UPLC-ESI-HRMS/MS. Among the characterized metabolites, SL with hirsutinolide and glaucolide skeletons showed the aforementioned diagnostic fragments and an ionization behavior that was similar to those observed during the water-sample combined injection. KEYWORDShirsutinolides and glaucolides, ESI-QTofMS n analysis, ESI adducts interaction, fragmentation mechanism, computational study Correction added on 22 May 2020, after online publication: the data in Tables 1, 2, 3, 5 and the citation numbering throughout the article were corrected post publication. /journal/jms 915 916 DA SILVA ET AL. Journal of MASS SPECTROMETRY RESULTS AND DISCUSSION ESI-HRMS/MS analysis of pure compoundsAs depicted in Table 1, ESI(+)-HRMS analysis by direct injection indicated that the SL 1-4 afforded as base peak the ions at m/z 445.1473 (1), m/z 487.1570 (2), m/z 419.1327 (3), and m/z 461.1422 (4), corresponding to [M+Na] + and suggesting a strong affinity for Na + . Moreover, protonated ions [M+H] + were not detected for the hirsutinolide skeletons ( compounds 1 and 3), whereas [M+H] + ions were observed in extremely low abundance for glaucolides 2 (m/z 465.1740, 15%) and 4 (m/z 439.1620, 2%).DA SILVA ET AL.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

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ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na⁺/H⁺ adducts interactions in complex mixture

et al. 2019

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“…A unique ion at m/z 224 was identified using the DART source most likely to be [TMDDD + NH 4 ] + as ammonium adducts can form within the helium plasma from atmospheric conditions. 46 A previous study conducted using DART attributed the ion at m/z 224 to [HMTD − H + NH 3 ] + and m/z 207 as [HMTD − H] + . 47 Subsequent research using MS/ MS of [TMDDD + NH 4 ] + identified a product ion at m/z 207 which further fragments to give the characteristic TMDDD ion at m/z 179.…”

Section: Resultsmentioning

confidence: 99%

Selectivity of Explosives Analysis with Ambient Ionization Single Quadrupole Mass Spectrometry: Implications for Trace Detection

Mathias,

Amerio-Cox,

Jackson

et al. 2023

J. Am. Soc. Mass Spectrom.

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Ambient ionization (AI) is a rapidly growing field in mass spectrometry (MS). It allows for the direct analysis of samples without any sample preparation, making it a promising technique for the detection of explosives. Previous studies have shown that AI can be used to detect a variety of explosives, but the exact gas-phase reactions that occur during ionization are not fully understood. This is further complicated by differences in mass spectrometers and individual experimental set ups between researchers. This study investigated the gas-phase ion reactions of five different explosives using a variety of AI techniques coupled to a Waters QDa mass spectrometer to identify selective ions for explosive detection and identification based on the applied ambient ionization technique. The results showed that the choice of the ion source can have a significant impact on the number of ions observed. This can affect the sensitivity and selectivity of the data produced. The findings of this study provide new insights into the gas-phase ion reactions of explosives and could lead to the development of more sensitive and selective AI-based methods for their detection.

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Exploiting the formation of adducts in mobile phases with ammonium fluoride for the enhancement of annotation in liquid chromatography-high resolution mass spectrometry based lipidomics

González-Riaño

Gradillas

Barbas

2021

Journal of Chromatography Open

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Energy decomposition analysis of the interactions in adduct ions of acetophenone and Na+, NH4+ and H+ in the gas phase

Cited by 3 publications

References 33 publications

ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na⁺/H⁺ adducts interactions in complex mixture

ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na⁺/H⁺ adducts interactions in complex mixture

Selectivity of Explosives Analysis with Ambient Ionization Single Quadrupole Mass Spectrometry: Implications for Trace Detection

Exploiting the formation of adducts in mobile phases with ammonium fluoride for the enhancement of annotation in liquid chromatography-high resolution mass spectrometry based lipidomics

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Energy decomposition analysis of the interactions in adduct ions of acetophenone and Na+, NH4+ and H+ in the gas phase

Cited by 3 publications

References 33 publications

ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na+/H+ adducts interactions in complex mixture

ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na+/H+ adducts interactions in complex mixture

Selectivity of Explosives Analysis with Ambient Ionization Single Quadrupole Mass Spectrometry: Implications for Trace Detection

Exploiting the formation of adducts in mobile phases with ammonium fluoride for the enhancement of annotation in liquid chromatography-high resolution mass spectrometry based lipidomics

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ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na⁺/H⁺ adducts interactions in complex mixture

ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na⁺/H⁺ adducts interactions in complex mixture