Effect of hydration and structure on the fragmentation of 2,2-(propane-1,3-diyl)bis(isoindoline-1,3-dione) and 2,2-(ethane-1,2-diyl)bis(isoindoline-1,3-dione) in electron impact ionization-mass spectrometry: A theoretical and experimental study

Yosefdad, Samiyeh; Valadbeigi, Younes; Bayat, Mohammad

doi:10.1016/j.molstruc.2019.127105

Cited by 3 publications

(1 citation statement)

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“…Hence, the amount of water vapor increases in the ionization region leading to hydration of the protonated forms of morphine and codeine. Hydration of the protonated compounds by water molecules reduces their fragmentation 45 . To interpret this observation, mono‐hydration of the protonated isomers Mor.H + ‐ b , Cod.H + ‐ b , and Theb.H + ‐ b was investigated theoretically.…”

Section: Resultsmentioning

confidence: 99%

Mechanism of atmospheric pressure chemical ionization of morphine, codeine, and thebaine in corona discharge–ion mobility spectrometry: Protonation, ammonium attachment, and carbocation formation

2020

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Atmospheric pressure chemical ionizations (APCIs) of morphine, codeine, and thebaine were studied in a corona discharge ion source using ion mobility spectrometry (IMS) at temperature range of 100 C-200 C. Density functional theory (DFT) at the B3LYP/6-311++G(d,p) and M062X/6-311++G(d,p) levels of theory were used to interpret the experimental data. It was found that in the presence of H 3 O + as reactant ion (RI), ionization of morphine and codeine proceeds via both the protonation and carbocation formation, whereas thebaine participates only in protonation. Carbocation formation (fragmentation) was diminished with decrease in the temperature. At lower temperatures, proton-bound dimers of the compounds were also formed. Ammonia was used as a dopant to produce NH 4 + as an alternative RI. In the presence of NH 4 + , proton transfer from ammonium ion to morphine, codeine, and thebaine was the dominant mechanism of ionization. However, small amount of ammonium attachment was also observed. The theoretical calculations showed that nitrogen atom of the molecules is the most favorable proton acceptor site while the oxygen atoms participate in ammonium attachment. Furthermore, formation of the carbocations is because of the water elimination from the protonated forms of morphine and codeine.

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Section: Resultsmentioning

confidence: 99%

Mechanism of atmospheric pressure chemical ionization of morphine, codeine, and thebaine in corona discharge–ion mobility spectrometry: Protonation, ammonium attachment, and carbocation formation

2020

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Insights into synthesis, reactivity, and biological activity of N-isoindoline-1, 3-diones heterocycles: a systematic literature review

Ou-Ichen,

Boussetta,

Ouchetto

et al. 2024

J IRAN CHEM SOC

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Transition-Metal-Catalyzed Decarbonylative Functionalization of Phthalimides

et al. 2022

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Phthalimide derivatives are prevalent in a wide array of biologically important molecules, including drugs, fungicides and anticancer molecules. Thus, catalytic methods that directly edit phthalimide moiety, in particular, decarbonylation and derivatization, could be strategically valuable for modification existing phthalimide molecular scaffolds. In recent years, considerable efforts have been devoted to emulating the transition-metal catalyzed phthalimides decarbonylative reaction. A set of elegant strategies including decarbonylative addition reactions with alkynes, alkenes, and benzynes, decarbonylative polymerization, alkylation, arylation, and protodecarbonylation have been demonstrated. This review aims to highlight these advances and discusses the mechanism issues, which will definitely further expand their applications and promote the developments in this field.

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Effect of hydration and structure on the fragmentation of 2,2-(propane-1,3-diyl)bis(isoindoline-1,3-dione) and 2,2-(ethane-1,2-diyl)bis(isoindoline-1,3-dione) in electron impact ionization-mass spectrometry: A theoretical and experimental study

Cited by 3 publications

References 29 publications

Mechanism of atmospheric pressure chemical ionization of morphine, codeine, and thebaine in corona discharge–ion mobility spectrometry: Protonation, ammonium attachment, and carbocation formation

Mechanism of atmospheric pressure chemical ionization of morphine, codeine, and thebaine in corona discharge–ion mobility spectrometry: Protonation, ammonium attachment, and carbocation formation

Insights into synthesis, reactivity, and biological activity of N-isoindoline-1, 3-diones heterocycles: a systematic literature review

Transition-Metal-Catalyzed Decarbonylative Functionalization of Phthalimides

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