1,8-Bis(dimethylamino)naphthalene
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Properties |
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| Name | Proton sponge |
| Name (IUPAC system) | 1,8-(dimethylamino)naphthalene |
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| Chemical formula | C14H18N 2 |
| Molecular weight | 214.3096 amu |
| CAS number | 20734-58-1 |
| Melting point | 321.0 K (47.8°C) |
| 1H-NMR(CCl4) | δ (ppm): 2.17(CH3), 6.74, 2.17(C10H8) |
| Acid dissociation constant:pKa | 12.34 |
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More information | |
| Properties | NIST WebBook |
| MSDS | Hazardous Chemical Database |
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Unless otherwise stated, all data was produced under conditions of standard temperature and pressure. | |
Proton-sponge is the general term for 1,8-(dimethylamino)naphthalene. It is a trademark of Aldrich Chemical Co., of Milwaukee, Wisconsin, USA. This compound is a kind of diamine group, in which two dimethylamine groups bond at the 1 and 8 positions of naphthalene. Proton-sponge has several very interesting properties; one is its very high basicity; another is its spectropic properties.
Proton-sponge has one of the highest Bronsted base values (acid dissociation constant: p’’K’’a = 12.34 in aqueous solution) of any organic compound. This property attributed to the relief of strain upon protonation and/or the strong interaction between the nitrogen lone pair1. Because of this property, Proton-sponge has been used in organic synthesis as a catalyst and in chemical synthesis as a strong nucleophilic chemical.
The spectropic properties of Proton-sponge are very interesting for researchers of molecular chemistry and have been researched for a long time. Proton-sponge emits a double fluorescence in various solutions due to the mixture of two ground-state species2.
Proton-sponge is methylated by using dimethyl-sulfuric acid. The p’’K’’a of trimethylated Proton-sponge is 6.43 in aqueous solution.