Methylpyridinium

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Methylpyridinium
1-Methylpyridinium.svg
Names
Preferred IUPAC name
1-Methylpyridin-1-ium
Other names
N-Methylpyridinium
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C6H8N/c1-7-5-3-2-4-6-7/h2-6H,1H3/q+1
    Key: PQBAWAQIRZIWIV-UHFFFAOYSA-N
  • InChI=1/C6H8N/c1-7-5-3-2-4-6-7/h2-6H,1H3/q+1
    Key: PQBAWAQIRZIWIV-UHFFFAOYAW
  • [n+]1(ccccc1)C
Properties
C6H8N+
Molar mass 94.134 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methylpyridinium is an ion with the formula C5H5NCH+3. It is the N-methylated derivative of pyridine. It confers no color to its salts. The ion is classified as a quaternary ammonium ion. [1]

Contents

Preparation and occurrence

Methylpyridinium is prepared by treating pyridine with dimethylsulfate: [2]

C5H5N + (CH3O)2SO2 → [C5H5NCH3]+CH3OSO−3

It is found in some coffee products. [3] It is not present in unroasted coffee beans, but is formed during roasting from its precursor chemical, trigonelline. [3]

Ionic liquid

The chloride salt of N-methylpyridinium behaves as an ionic liquid. Mixtures of that salt and zinc chloride have been characterised over the temperature range 150–200 °C (423–473 K). [4] [5] [6] [7]

See also

References

  1. ↑ Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2000). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. p. 558. doi:10.1002/14356007.a22_399. ISBN   9783527303854.
  2. ↑ E. A. Prill, S. M. McElvain (1935). "1-Methyl-2-Pyridone". Organic Syntheses. 15: 41. doi:10.15227/orgsyn.015.0041.
  3. 1 2 "Highly Active Compound Found In Coffee May Prevent Colon Cancer". ScienceDaily. Oct 15, 2003. Retrieved Oct 10, 2012.
  4. ↑ Simonis, L.; Coppe, C.; Glibert, J.; Claes, P. (1986). "Properties of mixtures of zinc chloride and N-methylpyridinium chloride in the molten state – I. Phase diagram and heats of mixing". Thermochimica Acta. 99: 223–232. Bibcode:1986TcAc...99..223S. doi:10.1016/0040-6031(86)85285-6.
  5. ↑ Claes, P.; Simonis, L.; Glibert, J. (1986). "Properties of mixtures of zinc chloride and N-methylpyridinium chloride in the molten state – II. Specific mass, electrical conductivity and viscosity". Electrochimica Acta. 31 (12): 1525–1530. doi:10.1016/0013-4686(86)87071-2.
  6. ↑ Claes, P. F.; Coppe, C. R.; Simonis, L. A.; Glibert, J. E. (1987). "Properties of mixtures of zinc chloride and N-methylpyridinium chloride in the molten state – III. Solubility of hydrogen chloride under atmospheric pressure and comparison with zinc chloride—N-ethylpyridinium bromide mixtures". Journal of Chemical and Engineering Data. 32 (1): 70–72. doi:10.1021/je00047a020.
  7. ↑ Marković, R.; Minić, D. M. (1997). "Conductometric and thermal studies of fused Zn(II) salts containing methyl substituted pyridinium cations". Materials Chemistry and Physics. 50 (1): 20–24. doi:10.1016/S0254-0584(97)80178-2.


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