Tetratsoli

Tetratsoli
Tunnisteet
CAS-numero 288-94-8
PubChem CID 67519
SMILES C1=NNN=N1[1]
Ominaisuudet
Molekyylikaava CH2N4
Moolimassa 70,066 g/mol
Sulamispiste 156 °C[2]
Tiheys 1,406 g/cm3[3]
Liukoisuus veteen Liukenee veteen

Tetratsoli (CN4H2) on typpeä sisältävä aromaattinen heterosyklinen orgaaninen yhdiste.

Ominaisuudet ja valmistus

Tetratsolin tautomeriset muodot

Tetratsolin heterosyklinen ja aromaattinen rengas koostuu yhdestä hiiliatomista ja neljästä typpiatomista. Tetratsoli esiintyy kahtena eri tautomerisena muotona 1H-tetratsolina ja 2H-tetratsolina[4] ja nämä eroavat siten onko vetyatomi sitoutunut 1- vai 2-asemassa sijaitsevaan typpiatomiin. Tautomeereista 1H-tetratsoli on vallitseva liuoksissa ja 2H-tetratsoli on susitumpi muoto kaasufaasissa.[5] Huoneenlämpötilassa tetratsoli on väritöntä kiteistä ainetta. Yhdiste on suhteellisen stabiili, mutta voi räjähtää kuumennettaessa yli 180 °C:n lämpötilaan[6]. Se liukenee hyvin veteen ja polaarisiin orgaanisiin liuottimiin kuten etanoliin ja asetoniin, mutta huonommin poolittomiin liuottimiin kuten bentseeniin tai dietyylieetteriin[2]. Tetratsolin pKa-arvo on noin 5, mikä tekee siitä yhtä happaman kuin useat karboksyylihapot.[4][5] se kykeneekin muodostamaan eräiden metallien kanssa suoloja, joissa esiintyy negatiivisesti varautunut tetratsolidi-ioni. Tetratsoli reagoi elektrofiilien kanssa joko 1- tai 2-asemassa sijaitsevalla typpiatomilla.[5]

Tetratsolia voidaan valmistaa vetysyanidin ja vetyatsidin tai amidratsonin ja typpihapokkeen välisellä reaktiolla[2]. Yhdistettä voidaan käyttää 5-aminotetratsolin kanssa autojen turvatyynyissä, koska se kuumentuessa voidaan saada kontrolloituessa räjähtämään vapauttaen typpikaasua[6].

Lähteet

  1. ↑ 1H-tetrazole – Substance summary PubChem. NCBI. Viitattu 4.9.2014.
  2. ↑ a b c Alén, Raimo: Kokoelma orgaanisia yhdisteitä: Ominaisuudet ja käyttökohteet, s. 908. Helsinki: Consalen Consulting, 2009. ISBN 978-952-92-5627-3
  3. ↑ William M. Haynes, David R. Lide, Thomas J. Bruno: CRC Handbook of Chemistry and Physics, s. 3.509. (93rd Edition) CRC Press, 2012. ISBN 978-1439880494 Kirja Googlen teoshaussa Viitattu 4.9.2014. (englanniksi)
  4. ↑ a b Jonathan Clayden, Nick Greeves, Stuart Warren: Organic Chemistry, s. 744. Oxford University Press, 2012. ISBN 978-0-19-927029-3 (englanniksi)
  5. ↑ a b c Theophil Eicher, Siegfried Hauptmann, Andreas Speicher: The Chemistry of Heterocycles, s. 23-25. John Wiley & Sons, 2013. ISBN 978-3-527-66986-8 Kirja Googlen teoshaussa Viitattu 4.9.2014. (englanniksi)
  6. ↑ a b John Arthur Joule, Keith Mills: Heterocyclic chemistry, s. 561. John Wiley and Sons, 2010. ISBN 978-1-4051-9365-8 Kirja Googlen teoshaussa Viitattu 4.9.2014. (englanniksi)

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