Pyrimidine

Pyrimidine
Pyrimidine molecule
Pyrimidine molecule
Names
Preferred IUPAC name
Pyrimidine[1]
Systematic IUPAC name
1,3-Diazabenzene
Other names
1,3-Diazine
m-Diazine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.479 Edit this at Wikidata
KEGG
MeSH pyrimidine
UNII
  • InChI=1S/C4H4N2/c1-2-5-4-6-3-1/h1-4H checkY
    Key: CZPWVGJYEJSRLH-UHFFFAOYSA-N checkY
  • InChI=1/C4H4N2/c1-2-5-4-6-3-1/h1-4H
    Key: CZPWVGJYEJSRLH-UHFFFAOYAT
  • n1cnccc1
Properties
C4H4N2
Molar mass 80.088 g mol−1
Density 1.016 g cm−3
Melting point 20 to 22 °C (68 to 72 °F; 293 to 295 K)
Boiling point 123 to 124 °C (253 to 255 °F; 396 to 397 K)
Miscible (25°C)
Acidity (pKa) 1.10[2] (protonated pyrimidine)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Pyrimidine (C4H4N2; /pɪˈrɪ.mɪˌdn, pˈrɪ.mɪˌdn/) is an aromatic, heterocyclic, organic compound similar to pyridine (C5H5N).[3] One of the three diazines (six-membered heterocyclics with two nitrogen atoms in the ring), it has nitrogen atoms at positions 1 and 3 in the ring.[4]: 250  The other diazines are pyrazine (nitrogen atoms at the 1 and 4 positions) and pyridazine (nitrogen atoms at the 1 and 2 positions).

In nucleic acids, three types of nucleobases are pyrimidine derivatives: cytosine (C), thymine (T), and uracil (U).

  1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 141. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Brown, H. C.; et al. (1955). Baude, E. A.; F. C., Nachod (eds.). Determination of Organic Structures by Physical Methods. New York, NY: Academic Press.
  3. ^ Gilchrist, Thomas Lonsdale (1997). Heterocyclic chemistry. New York: Longman. ISBN 978-0-582-27843-1.
  4. ^ Joule, John A.; Mills, Keith, eds. (2010). Heterocyclic Chemistry (5th ed.). Oxford: Wiley. ISBN 978-1-405-13300-5.

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