Comprehensive pKa table

Comprehensive pKa table - pKa's of Inorganic and Oxo-Acids...

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*Values <0 for H 2 O and DMSO, and values >14 for water and >35 for DMSO were extrapolated using various methods. 0.79 PEROXIDES pKa (DMSO) (DMSO) pKa pKa (DMSO) pKa's of Inorganic and Oxo-Acids 8.2 11.5 12.5 15.5 15.7 (11.1) (12.3) (1.6) (0.3) -14 (7.9) (12.9) (15) (1.8) (0.9) (32) (DMSO) cis -CO 2 H trans -CO 2 H R= 3.6, 10.3 3.77 -0.25 0.65 1.29 -8.0 11.6 -3.0, 1.99 1.9, 7.21 4.00 2.12, 7.21, 12.32 7.00 -1.7 15.7 -1.3 3.29 4.72 9.24 3.17 -0.98, 6.50 9.4 -2.6 -10 7.5 -9.00 9.23 INORGANIC ACIDS Chem 206 Substrate Substrate + + 1.92, 6.23 -12.4 -7.8 -6.2 -3.8 -2.05 -2.2 -2.6 2.1 + -1.8 -6.5 X= 1.68 2.66 2.86 2.86 3.12 4.76 4.2 o -O 2 NC 6 H 4 m -O 2 NC 6 H 4 p -O 2 NC 6 H 4 -(CH 3 ) 3 N + C 6 H 4 -OMeC 6 H 4 -ClC 6 H 4 -ClC 6 H 4 -ClC 6 H 4 2.17 2.45 3.44 2.94 3.83 3.99 1.37 -(CH 3 ) 3 N + C 6 H 4 3.43 4.47 4.25 3.02, 4.38 Substrate Substrate (13.7) (18.5) PROTONATED SPECIES CARBOXYLIC ACIDS (31.2) (27.9) (29.3) (23.5) (18.2) (29.4) 10.2 7.1 8.4 -OMeC 6 H 4 OH -O 2 NC 6 H 4 OH -O 2 NC 6 H 4 OH 9.95 (18.0) 2-napthol (17.1) (10.8) (19.1) ALCOHOLS 16.5 17.0 c -hex 3 COH 24.0 8.88 11.3 (20.1) pKa O OH R Ph Ph N OH N H Ph OH N + O OH O + H H Me N OH Ph O Me O OH X Me O + Me N + O OH Ph OH OH Ph Ph CH 3 OH O + H H Me S OH O O Ph S OH O S OH Me Me O + H Me Ph For a comprehensive compilation of Bordwell pKa data see: http://www.chem.wisc.edu/areas/reich/pkatable/index.htm H 2 O H 2 O H 2 O CH 3 CO 3 H MeOOH CF 3 SO 3 H (CF 3 ) 2 CHOH CF 3 CH 2 OH t -BuOH MeOH HOH H HO H CF 3 CCl 3 CHCl 2 HOOH H 2 SO 4 H 2 SO 3 HSCN H 3 PO 4 H 2 S H 3 O + H 2 O HNO 3 HNO 2 HN 3 NH 4 Cl H 2 CrO 4 HCN CH 3 SO 3 H HClO 4 HOCl HF HCl HBr B(OH) 3 CH 2 NO 2 CH 2 F CH 2 Cl CH 2 Br CH 2 I CH 3 C 6 H 5 i -PrOH C 6 H 5 OH (NH) H 2 O 9.3 (+5.55) N OH Me Me Me (+1.63)
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D.H. Ripin, D.A. Evans *Values <0 for H 2 O and DMSO, and values >14 for water and >35 for DMSO were extrapolated using various methods. 38
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This note was uploaded on 11/06/2010 for the course CHM CHM2120 taught by Professor Flynn during the Fall '09 term at University of Ottawa.

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Comprehensive pKa table - pKa's of Inorganic and Oxo-Acids...

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