The Protonation Site of para-Dimethylaminobenzoic Acid Using Atmospheric Pressure Ionization Methods View Full Text


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Article Info

DATE

2015-04

AUTHORS

Yunfeng Chai, Guofeng Weng, Shanshan Shen, Cuirong Sun, Yuanjiang Pan

ABSTRACT

The protonation site of para-dimethylaminobenzoic acid (p-DMABA) was investigated using atmospheric pressure ionization methods (ESI and APCI) coupled with collision-induced dissociation (CID), nuclear magnetic resonance (NMR), and computational chemistry. Theoretical calculations and NMR experiments indicate that the dimethyl amino group is the preferred site of protonation both in the gas phase and aqueous solution. Protonation of p-DMABA occurs at the nitrogen atom by ESI independent of the solvents and other operation conditions under typical thermodynamic control. However, APCI produces a mixture of the nitrogen- and carbonyl oxygen-protonated p-DMABA when aprotic organic solvents (acetonitrile, acetone, and tetrahydrofuran) are used, exhibiting evident kinetic characteristics of protonation. But using protic organic solvents (methanol, ethanol, and isopropanol) in APCI still leads to the formation of thermodynamically stable N-protonated p-DMABA. These structural assignments were based on the different CID behavior of the N- and O-protonated p-DMABA. The losses of methyl radical and water are the diagnostic fragmentations of the N- and O-protonated p-DMABA, respectively. In addition, the N-protonated p-DMABA is more stable than the O-protonated p-DMABA in CID revealed by energy resolved experiments and theoretical calculations. More... »

PAGES

668-676

References to SciGraph publications

  • 2011-02. Kinetic Control of Protonation in Electrospray Ionization in JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
  • 1971-06. A study of the effect of protonation on the electronic structure of the diatomic molecules BF, CO and N2 in THEORETICAL CHEMISTRY ACCOUNTS
  • 2013-07. Kinetic and Thermodynamic Control of Protonation in Atmospheric Pressure Chemical Ionization in JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/s13361-014-1069-7

    DOI

    http://dx.doi.org/10.1007/s13361-014-1069-7

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1045141334

    PUBMED

    https://www.ncbi.nlm.nih.gov/pubmed/25627246


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