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Related Experiment Videos

Ethyl (2-pyridylmethyl)phosphonate.

Lilianna Checińska1, Magdalena Małecka, Katarzyna Aranowska

  • 1Department of Crystallography and Crystal Chemistry, University of Łódź, Pomorska 149/153, 90-236 Łódź, Poland. lilach@uni.lodz.pl

Acta Crystallographica. Section C, Crystal Structure Communications
|January 11, 2005
PubMed
Summary

This study reveals that C8H12NO3P molecules exist as zwitterions, with charge delocalization across the pyridyl ring and the phosphonate group. Conformational and hydrogen-bonding features are detailed and compared to a related phosphonic acid.

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Area of Science:

  • * Chemical Crystallography
  • * Molecular Structure
  • * Supramolecular Chemistry

Background:

  • * Zwitterionic compounds are crucial in biological systems and materials science.
  • * Understanding charge distribution and hydrogen bonding is key to predicting molecular behavior.
  • * (2-Pyridylmethyl)phosphonic acid serves as a structural reference for comparison.

Purpose of the Study:

  • * To elucidate the crystal structure and electronic properties of the title compound (C8H12NO3P).
  • * To investigate the zwitterionic nature and charge delocalization within the molecule.
  • * To compare the conformational and hydrogen-bonding characteristics with (2-pyridylmethyl)phosphonic acid.

Main Methods:

  • * Single-crystal X-ray diffraction analysis.

Related Experiment Videos

  • * Analysis of electronic structure and charge distribution.
  • * Comparative structural analysis.

    • Main Results:

    • * The title compound crystallizes as a zwitterion with delocalized positive charge over the pyridyl ring.
    • * Partial delocalization of negative charge is observed within the phosphonate (O-P-O) system.
    • * Distinct conformational features and hydrogen-bonding patterns were identified and compared.

    Conclusions:

    • * The electronic structure of C8H12NO3P is characterized by significant charge delocalization, influencing its properties.
    • * The hydrogen-bonding network plays a critical role in stabilizing the zwitterionic form in the solid state.
    • * Structural comparison provides insights into the impact of specific functional groups on molecular assembly.