Hexaaza-18-crown-6

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]

Hexaaza-18-crown-6

Names
Other names 1,4,7,10,13,16-hexaazacyclooctadecane, hexacyclen
Identifiers
CAS Number	296-35-5
3D model (JSmol)	Interactive image
ChemSpider	38121
ECHA InfoCard	100.005.494
EC Number	206-042-8
PubChem CID	41779
CompTox Dashboard (EPA)	DTXSID70183778
InChI InChI=1S/C12H30N6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h13-18H,1-12H2 Key: RVJABZUDCPZPPM-UHFFFAOYSA-N
SMILES C1CNCCNCCNCCNCCNCCN1
Properties
Chemical formula	C12H30N6
Molar mass	258.414 g·mol^−1
Appearance	white solid
Melting point	201 °C (394 °F; 474 K)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319
GHS precautionary statements	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

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.