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Syntheses, conformations, and basicities of bicyclic triamines.

Thomas W Bell1, Heung-Jin Choi, William Harte

  • 1Department of Chemistry, University of Nevada, Reno, Nevada 89557-0020, USA. twb@unr.edu

Journal of the American Chemical Society
|October 2, 2003
PubMed
Summary
This summary is machine-generated.

Bicyclic triamines with a 1,5,9-triazacyclododecane ring show enhanced stability when monoprotonated due to hydrogen bonding. Shorter bridges do not provide this stabilization, as confirmed by NMR and computational studies.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Physical Chemistry

Background:

  • Synthesis of novel bicyclic triamines incorporating the 1,5,9-triazacyclododecane ring system.
  • Investigation of protonation states and their influence on molecular stability.

Purpose of the Study:

  • To synthesize and characterize bicyclic triamines with varying bridge lengths.
  • To investigate the stabilization effects of hydrogen-bonded networks in monoprotonated triamines.
  • To determine the energetic contributions of hydrogen bonds to molecular conformation and stability.

Main Methods:

  • Multistep organic synthesis of bicyclic triamine derivatives.
  • X-ray crystallography for structural elucidation.
  • Variable-temperature (1)H and (13)C NMR spectroscopy to measure activation free energies.
  • Computational studies (e.g., DFT) to analyze hydrogen bonding and conformational preferences.

Main Results:

  • Triamines with three-carbon bridges (1,5,9-triazabicyclo[7.3.3]pentadecanes) exhibit significant stabilization of their monoprotonated forms (>8 pK(a) units difference) due to robust hydrogen-bonded networks.
  • Triamines with one- or zero-carbon bridges show no enhanced stability in their monoprotonated states.
  • X-ray structures and computational data confirm the presence and strength of hydrogen-bonded networks, particularly in 15.HI.
  • NMR studies determined activation free energies for conformational inversion, providing estimates for bifurcated hydrogen bond strengths (e.g., 6.2 kcal/mol experimentally, 10.32 kcal/mol computationally for 16.HI).

Conclusions:

  • The length of the carbon bridge in bicyclic triamines critically influences the stability of their monoprotonated forms via intramolecular hydrogen bonding.
  • Three-carbon bridges effectively create stabilizing hydrogen-bonded networks involving bridgehead nitrogens.
  • Computational and experimental data provide quantitative insights into the strength and role of bifurcated hydrogen bonds in these systems.