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A solid-state NMR approach for distinguishing between RNH2 and RNH3+ sites.

Riley Nickles1, Emily C Heider2, James K Harper3

  • 1Brigham Young University, Department of Chemistry and Biochemistry, Provo, UT, 84602, USA.

Solid State Nuclear Magnetic Resonance
|June 25, 2025
PubMed
Summary
This summary is machine-generated.

This study introduces a method to determine the ionization state of solid organic materials by analyzing nitrogen-15 (15N) chemical shift tensors. This technique effectively differentiates between amine (R-NH2) and ammonium (R-NH3+) groups in various compounds.

Keywords:
(15)NChemical shift anisotropyChemical shift tensorsSolid-state NMRSpectral editing

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Area of Science:

  • Solid-state chemistry
  • Organic materials characterization
  • Spectroscopy

Background:

  • Accurate assignment of ionization states is crucial for characterizing solid-phase organic materials.
  • Solution phase pKa values are unreliable for solids due to environmental influences on ionization.
  • Distinguishing between amine (R-NH2) and ammonium (R-NH3+) groups is essential.

Purpose of the Study:

  • To develop and validate a method for distinguishing R-NH2 and R-NH3+ in solid organic materials.
  • To establish criteria for ionization state assignment based on experimental data.
  • To investigate factors influencing observed spectroscopic differences.

Main Methods:

  • Utilized experimental 15N chemical shift tensor principal values (δ11, δ22, δ33).
  • Analyzed 18 model compounds representing diverse chemical environments.
  • Calculated anisotropy values from the principal values of the 15N chemical shift tensors.

Main Results:

  • 15N sites as R-NH3+ exhibited anisotropies between 5 and 15 ppm.
  • 15N sites as R-NH2 showed anisotropies ranging from 14 to 115 ppm.
  • R-NH2 moieties were further classifiable into three distinct subgroups based on anisotropy.

Conclusions:

  • The method reliably distinguishes between R-NH2 and R-NH3+ based on 15N chemical shift tensor anisotropy.
  • Observed differences are attributed to variations in hydrogen bonding symmetry or aromatic ring attachment.
  • This spectroscopic approach provides a valuable tool for solid-state organic material analysis.