1,4,7-Trimethyl-1,4,7-triazacyclononane explained

1,4,7-Trimethyl-1,4,7-triazacyclononane is the aza-crown ether with the formula (CH2CH2NCH3)3. This colorless liquid is the N-methylated derivative of triazacyclononane (TACN), a face-capping tridentate ligand that is popular in coordination chemistry.

Although TACN is known for forming 2:1 "sandwich" complexes with many metal ions,[1] corresponding 2:1 complexes of Me3TACN are only known for Ag+,[2] Na+,[3] and K+.[4] This effect is mainly due to the greater bulk of Me3TACN, which requires ions with a larger ionic radius to accommodate two ligands.

Several related derivatives have been prepared with diverse substituents on nitrogen.[5] [6]

Notes and References

  1. 1,4,7-Triazacyclononane and N,N',N"-Trimethyl-1,4,7-triazacyclononane - Two Versatile Macrocycles for the Synthesis of Monomeric and Oligomeric Metal Complexes. Weighardt, Karl. 96871622. Pure and Applied Chemistry. 1988. 60. 4. 509–16. 10.1351/pac198860040509. free.
  2. Stockheim. Claudia. Wieghardt. Karl. Nuber. Bernhard. Weiss. Johannes. Flöurke. Ulrich. Haupt. Hans-Jürgen. 1991. Co-ordination chemistry of 1,4,7-triazacyclononane (L) and its N-methylated derivative (L) with silver(I) and mercury(II). The crystal structures of [AgL{{prime}} 2 ]PF 6 and [AgL{{prime}}(SCN)]]. J. Chem. Soc., Dalton Trans.. en. 6. 1487–1490. 10.1039/DT9910001487. 0300-9246.
  3. Everett. Matthew. Jolleys. Andrew. Levason. William. Pugh. David. Reid. Gillian. 2014. Unexpected neutral aza-macrocycle complexes of sodium. Chemical Communications. en. 50. 44. 5843–6. 10.1039/c4cc01407c. 24759888. 1359-7345. free.
  4. Dyke. John. Levason. William. Light. Mark E.. Pugh. David. Reid. Gillian. Bhakhoa. Hanusha. Ramasami. Ponnadurai. Rhyman. Lydia. 2015. Aza-macrocyclic complexes of the Group 1 cations – synthesis, structures and density functional theory study. Dalton Trans.. en. 44. 31. 13853–13866. 10.1039/C5DT01865J. 26115444. 1477-9226. free.
  5. Book: Inorganic Syntheses. Jason A. Halfen . William B. Tolman. C 2 -Symmetric 1,4-Diisopropyl-7- R -1,4,7-Triazacyclononanes . 1998. 32. 75–81. 10.1002/9780470132630.ch12. 9780470132630.
  6. 10.1071/CH02063. An Investigation into Alkenyl-Functionalized 1,4,7-Triazacyclononanes: Synthesis, Metal Complexation, and Attempted Olefin Metathesis. 2002. Baker. M. V.. Brown. D. H.. Skelton. B. W.. White. A. H.. Australian Journal of Chemistry. 55. 10. 655.

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