Chemistry:Hexaaza-18-crown-6

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Hexaaza-18-crown-6
Hexaaza-crown-6.svg
Names
Preferred IUPAC name
1,4,7,10,13,16-Hexaazacyclooctadecane
Other names
hexacyclen
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 206-042-8
Properties
C12H30N6
Molar mass 258.414 g·mol−1
Appearance white solid
Melting point 201 °C (394 °F; 474 K)
Hazards
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319
P264, P280, P302+352, P305+351+338, P321, P332+313, P337+313, P362
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Hexaaza-18-crown-6 is the macrocyclic ligand with the formula (CH2CH2NH)6. A white solid, this compound has attracted attention as the N6-analogue of 18-crown-6. It functions as a hexadentate ligand in coordination chemistry. It is the parent hexaaza-crown ether.[1]

Structure of [Co(III)(hexaaza-18-crown-6)]3+.[2]

Its protonated derivatives bind anions via multiple hydrogen bonds.[3]

References

  1. Atkins, T. J.; Richman, J. E.; Oettle, W. F. (1978). "1,4,7,10,13,16-Hexaazacyclooctadecane". Org. Synth. 58: 86. doi:10.15227/orgsyn.058.0086. 
  2. Morooka, M.; Ohba, S.; Toriumi, K. (1992). "Electron-Density Distribution in Crystals of 1,4,7,10,13,16-Hexaazacyclooctadecanecobalt(III) Trichloride, meso-[Co(hexaen)]Cl3 at 106 K". Acta Crystallographica Section B: Structural Science 48 (4): 459–463. doi:10.1107/S0108768192002714. 
  3. Fonari, Marina S.; Ganin, Eduard V.; Gelmboldt, Vladimir O.; Basok, Stepan S.; Luisi, Brian S.; Moulton, Brian (2008). "Binding of Fluoro-Containing Anions to Hexaazamacrocyclic Ligand: Competitive Interactions of Fluoride and Tetrafluoroborate Anions with Hexaprotonated [18]aneN6". Inorganic Chemistry Communications 11 (5): 497–501. doi:10.1016/j.inoche.2008.01.028.