We are analyzing https://link.springer.com/article/10.1007/s13361-013-0626-9.

Title:
Kinetic and Thermodynamic Control of Protonation in Atmospheric Pressure Chemical Ionization | Journal of The American Society for Mass Spectrometry
Description:
For p-(dimethylamino)chalcone (p-DMAC), the N atom is the most basic site in the liquid phase, whereas the O atom possesses the highest proton affinity in the gas phase. A novel and interesting observation is reported that the N- and O-protonated p-DMAC can be competitively produced in atmospheric pressure chemical ionization (APCI) with the change of solvents and ionization conditions. In neat methanol or acetonitrile, the protonation is always under thermodynamic control to form the O-protonated ion. When methanol/water or acetonitrile/water was used as the solvent, the protonation is kinetically controlled to form the N-protonated ion under conditions of relatively high infusion rate and high concentration of water in the mixed solvent. The regioselectivity of protonation of p-DMAC in APCI is probably attributed to the bulky solvent cluster reagent ions (SnH+) and the analyte having different preferred protonation sites in the liquid phase and gas phase.
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Topics {✒️}

month download article/chapter nan hu & yuanjiang pan β-unsaturated aromatic ketones unexpected gas-phase reactivity gas-phase cation attachment p-hydroxybenzoic acid investigated acid–base tautomerization equilibria phase-separation multiphase flow collision-induced dissociation protonated p-aminobenzoic acid photoelectron spectra o-protonated p-dmac stereoisomeric gas-phase ions tandem mass spectrometry n-protonated ion dramatic temperature dependence chemistry privacy choices/manage cookies protonation process full article pdf gas-phase structures liquid-phase structures electrospray ionization afford p-hydroxybenzoic acid β-unsaturated enone protonated 4-aminobenzoic acid gas-phase acidity gas-phase acidities ir spectroscopy relative acidity scale microscopic proton ionization o-protonated ion solution-phase structure mass spectrometry european economic area related subjects carbon-13 resonance investigation 13c nmr determination stepwise radical expulsions neutral species lost strained transition states national science foundation carboxy-protonated ion gas-phase deprotonation stable carbonium ions quasi-molecular ions column pressure highest proton affinity high infusion rate ray

Questions {❓}

Are carboxyl groups the most acidic sites in amino acids?
Deprotonation of p-hydroxybenzoic acid: does electrospray ionization sample solution or gas-phase structures?
Does electrospray ionization produce gas-phase or liquid-phase structures?
Infrared multiphoton dissociation spectroscopy study of protonated p-aminobenzoic acid: does electrospray ionization afford the amino- or carboxy-protonated ion?

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         description:For p-(dimethylamino)chalcone (p-DMAC), the N atom is the most basic site in the liquid phase, whereas the O atom possesses the highest proton affinity in the gas phase. A novel and interesting observation is reported that the N- and O-protonated p-DMAC can be competitively produced in atmospheric pressure chemical ionization (APCI) with the change of solvents and ionization conditions. In neat methanol or acetonitrile, the protonation is always under thermodynamic control to form the O-protonated ion. When methanol/water or acetonitrile/water was used as the solvent, the protonation is kinetically controlled to form the N-protonated ion under conditions of relatively high infusion rate and high concentration of water in the mixed solvent. The regioselectivity of protonation of p-DMAC in APCI is probably attributed to the bulky solvent cluster reagent ions (SnH+) and the analyte having different preferred protonation sites in the liquid phase and gas phase.
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            Analytical Chemistry
            Biotechnology
            Organic Chemistry
            Proteomics
            Bioinformatics
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      headline:Kinetic and Thermodynamic Control of Protonation in Atmospheric Pressure Chemical Ionization
      description:For p-(dimethylamino)chalcone (p-DMAC), the N atom is the most basic site in the liquid phase, whereas the O atom possesses the highest proton affinity in the gas phase. A novel and interesting observation is reported that the N- and O-protonated p-DMAC can be competitively produced in atmospheric pressure chemical ionization (APCI) with the change of solvents and ionization conditions. In neat methanol or acetonitrile, the protonation is always under thermodynamic control to form the O-protonated ion. When methanol/water or acetonitrile/water was used as the solvent, the protonation is kinetically controlled to form the N-protonated ion under conditions of relatively high infusion rate and high concentration of water in the mixed solvent. The regioselectivity of protonation of p-DMAC in APCI is probably attributed to the bulky solvent cluster reagent ions (SnH+) and the analyte having different preferred protonation sites in the liquid phase and gas phase.
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         Analytical Chemistry
         Biotechnology
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         Proteomics
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