1,4,7-triazonane

Also known as tacn, 1,4,7-triazacyclononane, [9]aneN₃

1,4,7-Triazacyclononane, known as "TACN" which is pronounced "tack-en," is an aza-crown ether with the formula (C2H4NH)3. TACN is derived, formally speaking, from cyclononane by replacing three equidistant CH2 groups with NH groups. TACN is one of the oligomers derived from aziridine, C2H4NH. Other members of the series include piperazine, C4H8(NH)2, and the cyclic tetramer 1,4,7,10-tetraazacyclododecane.

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Chemical data

Formula: C6H15N3
Molecular weight: 129.2 g/mol
IUPAC name: 1,4,7-triazonane
SMILES: C1CNCCNCCN1
InChIKey: ITWBWJFEJCHKSN-UHFFFAOYSA-N
XLogP: -1.9
Polar surface area: 36.1 Å²
H-bond donors: 3
H-bond acceptors: 3
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 129.126597

Show 3 more facts

Commons category: 1,4,7-Triazacyclononane
canonical SMILES: C1CNCCNCCN1
chemical formula: C₆H₁₅N₃

Sources (2)

via Wikidata · CC0

~3 min read

Encyclopedic overview

4 sections

Contents

Synthesis
Coordination chemistry
Illustrative complexes
References

==Synthesis== The ligand is prepared from diethylene triamine as follows by macrocyclization using ethyleneglycol ditosylate. H2NCH2CH2NHCH2CH2NH2 + 3 TsCl → Ts(H)NCH2CH2N(Ts)CH2CHH2N(H)Ts + 3 HCl Ts(H)NCH2CH2N(Ts)CH2CH2N(H)Ts + 2 NaOEt → Ts(Na)NCH2CH2N(Ts)CH2CH2N(Na)Ts Ts(Na)NCHH2CH2N(Ts)CH2CH2N(Na)Ts + TsOCH2CH2OTs + → [(CH2CH2N(Ts)]3 + 2 NaOTs [(CH2CH2N(Ts)]3 + 3 H2O → [CH2CH2NH]3 + 3 HOTs

Excerpted from Wikipedia’s “1,4,7-triazonane” article, available under the CC BY-SA 4.0 licence.