ADVANCES IN TETRAZOLE CHEMISTRY IN RUSSIA

V.A. Ostrovskii (all other questions, proposals or information) , Michael Yudintceff (web-master)

St.-Petersburg State Institute of Technology , 198013, St.Petersburg, Russia

Acid-Base Properties of Tetrazoles

Hammett and Similar (pKa and pKKH+) Correlations for Tetrazoles

 

Series

pKR = r s x + pKo

Lit.

5-R- tetrazoles

pKa = -6.65s p + 4.46;

pKKH+=-7.83s p - 2.28;

pKa = 0.78 pKKH+ + 6.37;

[1]

5-Aryltetrazole

pKa =-1.27s + 4.40;

pKKH+=-1.80s - 2.24;

[2]

1-Aryltetrazoles

pKKH+=-0.85s n - 3.59;

[3]

1-(Aryltetrazole-5-yl)-1’-Aryltetrazoles (N,N’-Diarylditetrazoles)

pKKH+=-0.85s n - 7.47;

[4]

1-Aryl-5-Methyltetrazoles;

pKKH+=-1.17s I - 1.96;

[5]

1-Aryl-5-Phenyltetrazoles

pKKH+=-1.20s - 2.74;

[3]

1-Methyl-5-Aryltetrazoles

pKKH+=-1.63s - 2.43;

[6]

2-Methyl-5-Aryltetrazoles

pKKH+=-1.25s - 3.19;

[6]

 

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  1. V.A.Ostrovskii, G.I.Koldobskii, N.P.Shirokova, V.S.Poplavskii, Khim.Geterotsikl.Soedin., No4, 559-562 (1981).
  2. V.A.Ostrovskii, G.I.Koldobskii, N.P.Shirokova, I.Yu.Shirobokov, B.V.Gidaspov, Zh.Org.Khim. 14, No8, 1607-1701 (1978);V.N.Streltsova, Shirokova N.P., G.I. Koldobskii, B.V.Gidaspov, Zh.Org.Khim. 10, 1081-1085 (1974).
  3. V.A.Ostrovskii, G.I.Koldobskii, B.V.Gidaspov, E.N.Osokina, Zh.Org.Khim. 13, No11, 2421-2425 (1977).
  4. V.A.Ostrovskii, G.I.Koldobskii, E.N.Osokina, Zh.Org.Khim. 32, in press (1996).
  5. N.D.Agibalova A.S. Enin, G.I. Koldobskii, B.V.Gidaspov, T.N.Timofeeva, Zh.Org.Khim. 8, 2414-2418 (1974).
  6. A.V.Moskvin, V.A.Ostrovskii, I.Yu.Shirobokov, G.I.Koldobskii, B.V.Gidaspov, Zh.Org.Khim. 14, No11, 2440-2444 (1978).
  7. See also to: G.I.Koldobskii,V.A.Ostrovskii,B.V.Gidaspov,(Review), Khim.Geterotsikl.Soedin.,No7, 867-879 (1980).