D H. Ripin, D A. Evans Ka's of Inorganic and OXo-Acids Chem 206 Substrate pKa H2o(DMSO) Substrate pKa H2O(DMSO) Substrate pKa H2o(DMSo) Substrate pKa H2O(DMSO) INORGANIC ACIDS CARBOXYLIC ACIDS ALCOHOLS PROTONATED SPECIES 157(312) 1554(27.9) 2S 700 476(123) 16.5(293) CHaNO 168 -9.00(0.9) BUOH 17(294) 7.8 8.0(1.8) CH2CI 2.86 C-hex3 COH CH2Br 2.86 125(235) 3.12 (CF3)2CHOH (17.9) HOCI CsHSOH 9.95(180) CIOE 10 0.65 -6.5 -0.25 m-O2NCBH 94(129) pO2NC6H4OH714(108) 8 472(7.9) 4.2(11 //p-oMeCgH4OH 10.20(19.1)Me Me 6,103 2-napthol (171) 0-O2NCBH4 2.17 H2SO 19,721 m-O2NCSH4 2.45 oXIMES HYDROXAMIC ACiDs 2.2 H2SO4 3.0.199 p-O2NCBH4 3 0-CICSH4 294 113(20.1) 2.12,7.21, m-CICSHa 3.83 HNO 888(137) 079 HNO2 0-(CH3N'ceH4137 H2crO4 0.98,650 p-(CH3)3N*C6H4 3.43 (185) suLFINIC sULFoNIC aciDs 26(1.6) CF3SO3H 14(0.3) PEROXIDES 924 4.25 11.5 B(OH)3 trans-CO2H 3.02 438 CH3 CO3H HOOH 11.6 CIS-CO2H 1.92,623 values <0 for H2O and DMSO, and values >14 for water and >35 for DMSo were extrapolated using various methodsOH Ph OH + Ph CH3 OH + S OH Me Me + 15.7 (31.2) 15.54 (27.9) t-BuOH 12.5 (23.5) (CF3)2CHOH C6H5OH m-O2NC6H4OH 8.35 p-O2NC6H4OH 7.14 (10.8) p-OMeC6H4OH 10.20 (19.1) 2-napthol (17.1) 16.5 (29.3) Ph Ph N OH 11.3 (20.1) N OH Ph O Me (18.5) O N H Ph OH 8.88 (13.7) (17.9) 17 (29.4) 9.95 (18.0) R OH O N + OH O + H Me H O X OH Me O + Me H N + O Ph OH O + H Me S OH O O Ph S OH O O + H Ph Me H (DMSO) H2O (DMSO) H2O (DMSO) 2O CH3CO3H MeOOH CF3SO3H (DMSO) H HO H CF3 CCl3 CHCl2 HOOH H2SO4 H2SO3 HSCN H3PO4 H2S H3O + H2O HNO3 HNO2 HN3 NH4Cl H2CrO4 HCN CH3SO3H HClO4 HOCl HF HCl HBr B(OH)3 CH2NO2 CH2F CH2Cl CH2Br CH2I CH3 C6H5 H2O D.H. Ripin, D.A. Evans *Values <0 for H2O and DMSO, and values >14 for water and >35 for DMSO were extrapolated using various methods. 0.79 SULFINIC & SULFONIC ACIDS PEROXIDES pKa pKa pKa pKa's of Inorganic and Oxo-Acids 8.2 11.5 (11.1) (12.3) (1.6) -14 (0.3) (7.9) (12.9) (15) (1.8) (0.9) (32) cis-CO2H trans-CO2H 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-O2NC6H4 m-O2NC6H4 p-O2NC6H4 o-(CH3 )3N +C6H4 p-OMeC6H4 p-ClC6H4 o-ClC6H4 m-ClC6H4 2.17 2.45 3.44 2.94 3.83 3.99 1.37 p-(CH3 )3N +C6H4 3.43 4.47 4.25 3.02, 4.38 Substrate Substrate CARBOXYLIC ACIDS ALCOHOLS PROTONATED SPECIES c-hex3COH 24 OXIMES & HYDROXAMIC ACIDS pKa