Tröger's base
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Ball-and-stick models of the two enantiomers of Tröger's base
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| Names | |
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IUPAC name
2,8-Dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine
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| Other names
Troeger's base
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.150.499 |
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PubChem CID
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| Properties | |
| C17H18N2 | |
| Molar mass | 250.35 g·mol−1 |
| Melting point | 135–6 °C (275–43 °F; 408–279 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Tröger's base is an organic compound with the formula (CH3C6H4NCH2)2CH2. It is a white solid that is soluble in polar organic solvents. It is a diamine, which exhibits chirality due to the presence of two bridgehead stereogenic nitrogen atoms. The compound is of historic interest.
The compound was first synthesised in 1887 from p-toluidine and formaldehyde in acid solution by Julius Tröger. It can also be prepared with DMSO and hydrochloric acid or hexamethylene tetraamine (HMTA) as formaldehyde replacement.
The reaction mechanism with DMSO as methylene donor for this reaction is similar to that of the Pummerer rearrangement. The interaction of DMSO and hydrochloric acid yields an electrophilic sulfenium ion that reacts with the aromatic amine in an electrophilic addition. Dimethyl sulfide is eliminated and the resulting imine reacts with a second amine. Sulfenium ion addition and elimination is repeated with the second amino group and the imine group reacts in an intramolecular electrophilic aromatic substitution reaction. Imine generation is repeated a third time and the reaction concludes with a second electrophilic substitution to the other aromat.
The molecule can be considered a molecular tweezer because the bicyclic skeleton forces the molecule in a rigid locked conformation with the aromatic rings in proximity. When the methyl groups are replaced by pyridine amide groups a host-guest chemistry interaction can take place between the Tröger's base and an aliphatic dicarboxylic acid. It is found that the cavity dimensions are optimal for inclusion of suberic acid but that with a longer acid sebacic acid or a shorter acid adipic acid the interaction is less favorable.
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