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of Inorganic and Substrate pKa H2O (DMSO) INORGANIC ACIDS (32) 15 H2S 7 HBr (0) HCl 3 HOCl 7 H2O (DMSO) O X (1) (15) HClO4 HCN 9 (12) HN3 4 (7) OH CH3 CH2NO2 CH2F CH2Cl CH2Br CH2I CHCl2 CCl3 CF3 H HO C6H5 4 (12) 1 2 2 2 3 1 0 3 3, 10 4 (11) 2 HSCN 4 H2SO3 1, 7 2 H2SO4 1 3 2 3 3 HNO3 2, 7, 12 HNO2 3 H2CrO4 6 1 3 CH3SO3H (1) CF3SO3H (0) NH4Cl 9 B(OH)3 HOOH H3PO4 Substrate CARBOXYLIC ACIDS H2O HF pKa Substrate 4 pKa H2O (DMSO) ALCOHOLS Substrate O 15 (31) MeOH 15 Ph 16 (27) (29) 17 (29) Ph 24 CF3CH2OH 12 (23) 9 (18) 9 (18) (CF3)2CHOH C6H5OH 8 7 10 Ph OH OH Ph CH3 Ph Ph (10) (19) Me 11 1, 6 Me H H H OH OH 11 (20) S Me Me Ph OH N O H OH N OH 8 (13) (NH) (18) 0 Me N Me OH Me Me SULFINIC SULFONIC ACIDS O 9 Me OH 4 3, 4 Me H (17) PEROXIDES H H O Ph OH OH OXIMES HYDROXAMIC ACIDS N pKa H2O (DMSO) PROTONATED SPECIES HOH O R Chem 206 MeOOH 11 CH3CO3H 8 Me O S OH O Ph S 2 OH for H2O and DMSO, and values for water and for DMSO were extrapolated using various methods. For a comprehensive compilation of Bordwell pKa data see: pKa Table 1:43 PM D. Ripin, D. Evans pKa H2O Substrate (DMSO) Substrate pKa PROTONATED NITROGEN 9 10 3 (10) 11 10 (9) 2H 4 (3) 5 (2) 0 4 8 H2O (DMSO) Quinuclidine 11 Me Me H2N N (26) AMIDES CARBAMATES (9) H (23) CH3 15 (25) NH2 Ph (23) CF3 (17) (urea) NH2 (26) OEt (24) 8 O morpholine R 7 NO2 O2N NH3 NO2 O Et H DABCO O 2, 8 (2, 8) N H 6, 9 3 3 Proton Sponge 3 12 7) (21) O O Ac2NH 8 O NH ( )n O (20) O NH Ph (17) R N H NSO2Ph NH2 H N H N GUANIDINIUM, IDES, Me2N (13) NMe2 O Ph NNH2 Ph DBU (26) (12) (estimate) N H N H N H 9 NH HN H (PPTS) Me Cl, H 6 O N N (19) N (13) O (24) S (27) S H (29) Me NMe 5 (3) (0) H 4 O NH NH N (12) N (18) (4) 6 H Me R 0 for H2O and DMSO, and values for water and for DMSO were extrapolated using various methods. (15) NH N H H NH (18) X S DMAP Me2N N HN N (23) NH O (14) S (11) (17) PROTONATED HETEROCYCLES (16) N (11) O (24) X S (13) N H X PhSO2NHNH2 PhNHNHPh H N N Me (18) (20) N (21) NHNH2 R O (17) (15) Me Ph HETEROCYCLES (17) R Me Ph (16) CF3 6 (9) MeSO2NHPh (12) RSO2NH2 O 1 (24) 2 (26) (14) 8 (13) (NH) OH SULFONAMIDE N Bn O NH O NH O H 12 (20) Ph O NH pKa H2O (DMSO) Substrate HYDROXAMIC ACID AMIDINES IMIDES HN3 4 (7) NH3 (41) 38 (36 THF)) 26(THF) (30) TMS2NH PhNH2 (30) Me Ph2NH (25) Me NCNH2 (16) NH (37) NH (44) O Morpholine pKa H2O (DMSO) Substrate AMINES 5 H Chem 206 of Nitrogen Acids Me Me (16) N H Me For a comprehensive compilation of Bordwell pKa data see: pKa Table 1:43 PM (24) of CH bonds at Nitrile, Heteroaromatic, and Sulfur Substituted Carbon D. Ripin, D. Evans pKa H2O (DMSO) Substrate NITRILES NC (31) (32) (21) (10) 11 (17) (13) (11) (28) (20) (20) (12) MeSCH2SO2Ph (23) PhSCHPh2 (26) (PhS)3CH (22) (PrS)3CH (31) N N (28) Ph (26) Ph (23) Ph (25) O S (30) Ph (30) Ph (35) (29) (29) O Ph S X H Ph SOPh (33) (27) (18) O Ph (24) S CHPh2 SULFONIUM Ph (18) (16) CH2Ph SULFIMIDES SULFOXIMINES Ph Ph CO2Me CN RSCH2CN Me Et (30) (20) (19) (24) (24) (23) (22) (26) BuSH (17) (10) PhSH S Ph O Ph O Ph O Ph H CH3 Ph CCH CCPh COPh COMe OPh CN NO2 SMe SPh SO2Ph PPh2 O Ph S S S (22) CHPh2 O S (27) (30) Me (24) CF3 O (33) CF3 O Me NMe Me (14) Me NTs O CH2Cl CF3 Et S (31) Me O (18) Me O (21) S O (26) S O (20) O S (32) Et (PhSO2)2CH2Me for H2O and DMSO, and values for water and for DMSO were extrapolated using various methods. pKa Table 1:44 PM (29) (31) (31) (23) (22) (20) (22) (17) (11) (12) (27) (19) (12) (7) (23) (20) (12) (20) O S NTs S X O R Me O O S Ph NTs X X Me S N S H Ph SPh S (30) O S (PhS)2CHPh Ph Me Me (30) S H SULFONES O (30) (20) (18) (16) (11) (30) (20) (11) (24) S Substrate pKa H2O (DMSO) SULFOXIDES PhSCH2X Ph CN COCH3 COPh NO2 SPh SO2Ph SO2CF3 POPh2 pKa H2O (DMSO) Substrate SULFIDES X H CH3 Ph COPh CONR2 CO2Et CN OPh SPh SO2Ph pKa H2O (DMSO) Substrate Chem 206 (14) D. H. Ripin, D. A. Evans of CH bonds at Heteroatom Substituted Carbon References pKa H2O (DMSO) Substrate ETHERS CH3OPh MeOCH2SO2Ph (30) PhOCH2SO2Ph (27) PhOCH2CN (28) O (22) Ph NITRO RNO2 2 9 (22) (21) (6) CH3 CH2Me CHMe2 CH2Ph CH2Bn (7) PHOSPONATES PHOSPHINE OXIDES SELENIDES (18) Ph PhSeCHPh2 (27) (PhSe)2CH2 (31) PhSeCH2Ph (31) (27) O Ph2P AMMONIUM CN SO2Ph COPh CO2Et CONEt2 (20) (24) (17) (16) (16) (12) (16) (11) (7) (7) O2N X Ph (27) CN CO2Et (16) Cl SiMe3 (18) (26) (28) 3 (26) 4 (17) 5 6 (16) (17) (15) 7 X SPh CN (24) (16) N Ph PHOSPHINES Ph2PCH2PPh2 (29) Ph2PCH2SO2Ph (20) Ph JACS 97, 7007 (1975) JACS 97, 7160 (1975) JACS 97, 442 (1975) JACS 105, 6188 (1983) JOC 41, 1883 (1976) JOC 41, 1885 (1976) JOC 41, 2786 (1976) JOC 41, 2508 (1976) JOC 42, 1817 (1977) JOC 42, 321 (1977) JOC 42, 326 (1977) JOC 43, 3113 (1978) JOC 43, 3095 (1978) JOC 43, 1764 (1978) JOC 45, 3325 (1980) JOC 45, 3305 (1980) JOC 45, 3884 (1980) JOC 46, 4327 (1981) JOC 46, 632 (1981) JOC 47, 3224 (1982) JOC 47, 2504 (1982) Acc. Chem. Res. 21, 456 (1988) Unpublished results of F. Bordwell Water: IMINES (20) (19) (14) n (EtO)2P REFERENCES DMSO: CH2SPh CH2SO2Ph CH2COPh O O PhSe pKa H2O (DMSO) Substrate PHOSPHONIUM (49) MeO pKa H2O (DMSO) Substrate Chem 206 (24) Ph Oxime ethers are 10 pka units less acidic than their ketone counterparts Streitwieser, JOC 1991, 56, 1989 Advanced Org. Chem., 3rd Ed. J. March (1985) Unpublished results of W. P. Jencks THF: JACS 110, 5705 (1988) See cited website below for additional data for H2O and DMSO, and values for water and for DMSO were extrapolated using various methods. For a comprehensive compilation of Brodwell pKa data see: pKa Table 1:45 PM pKa Data Compiled R. Williams pKa Values INDEX Inorganic 2 Phenazine 24 Phosphates 3 Pyridine 25 Carboxylic acids 4, 8 Pyrazine 26 Aliphatic 4, 8 Aromatic 7, 8 Quinoline 27 Phenols 9 Quinazoline 27 Alcohols and oxygen acids 10, 11 Quinoxaline 27 Amino Acids 12 Special Nitrogen Compounds 28 Peptides 13 Hydroxylamines 28 Nitrogen Compounds 14 Hydrazines 28 Aliphatic amines 15, 17, 19 Semicarbazones 28 Cyanoamines 16 Amidoximes 28 Anilines 17, 18, 20 Thiols 29 Nucleosides 21 Carbon Acids 30,31 Special Table Heterocycles 22 Indicators 31 Acridine 23 References Benzoquinoline 24 Cinnoline 23 Hydantoin 24 Imidazole 24 For complex chelating agents, see also reference 77. Note. This document was compiled W. Jencks and has been added to F. Westheimer pKa Data Compiled R. Williams ACIDS Compound pK Ref. AgOH Al(OH)3 As(OH)3 H3 AsO 4 H2 AsO 4 HAsO 4 As 2 O 3 H3 AsO 3 H3 BO 3 H2 B4 O 7 HB4 O 7 Be(OH) 2 HBr HOBr HOCl HClO2 HClO3 HClO4 CH3 SO 3 H HCN H2 CO 3 HCO 3 H2 CrO4 HCrO4 HOCN HZ H2 GeO3 Ge(OH)4 HI HOI HIO3 H4 IO6 H5 IO6 HMnO4 NH3 NH4 HN3 HNO2 HNO3 N2 H5 H2 N2 O 2 H2 N2 O 2 H2 OsO 5 H2 O H3 O Pb(OH)2 3 11 9 2, 7, 13 0 4 9 3 8 7, 7 2 9 6, 3 3 8, 12 8, 12 11 0 6 1, 1, 8 3 7 11 12 15 6 (10) 4 28 28 28 77 77 4 28 34 34 4 31 28 28, 33 28 28 31 31 34 34, 32 30 2, 30 34 77 34, 78 28 31 28 28 34 34, 28 30 77 77 28 28 77 34 34 34 none none 4 (78) H3 PO 2 H2 PO 4 HPO 4 _ H3 PO 3 H2 PO 3 H4 P 2 O 7 H3 P 2 O 7 H2 P 2 O 7 HP2 O 7 HReO4 HSCN H2 SeO3 HSeO3 H2 SeO4 HSeO4 H3 SiO 3 H2 SO 3 H2 SO 4 HSO 3 HSO 4 H2 S2 O 4 H2 Se H2 S HSbO 2 HTe H2 Te H2 TeO 3 Te(OH) 6 H2 VO 4 HVO4 H2 CrO4 HOCN HSCN H3 PO 2 H3 PO 4 H2 S2 O 3 H3 AuO3 H3 GaO 3 H5 IO6 H4 V6 O 17 H2 NSO 3 H 2, 2 4 2, 8, 8 Strong, 2 2 10 1, 7, 1 1 11 5 2, 11 2, 8 6, 8 8 14 0 3 0 1 13, 16 10, 11 3, 6, 15 (see above!) 1 1 Indicates a thermodynamic value. 28 77 77 28 77 77 77 77 77 30 34 28 77 28 34 34 28, 77 28 77 77 29 77 77 77 77 34 34 34, 78 28 28 30 30 77 77 77 77 77 77 78 78 78 78 80 fluorophosphate 0, 4 56 Phosphonates (Ref. 2) X X(CH 2)PO 3H 2 2 7 1 5 X(CH 2) 2PO3H 2 2 7 2 7 X(CH 2) 4PO3H 2 2 7 X(CH 2) 5PO3 H2 2 7 X(CH 2) 6PO2H 2 2 7 X(CH 2) 10PO2H 2 8 Phosphines in acetonitrile, see ref. 89. CARBOXYLIC ACIDS Aliphatic Compound pK Acetoacetic 3 Acetopyruvic 2, 7 (enol) Aconitic, trans2, 4 Betaine 1 Citric 3, 4, 5 Crotonic 4 Dihydroxyfumaric 1 2, 2 tetraacetic 6, 10 Formic Fumaric 3, 4 Glyceric 3 Glycollic 3 Glyoxylic 3 Homogentistic 4 valeric 2 Lactic 3 Maleic 1, 6 Malic 3, 5 Oxaloacetic 2 2, 4 Protocatechuic 4 Pyruvic 2 Tartaric 2, 4 or 2, 4 meso 3, 4 Vinylacetic 4 Ref. 6 6 6 6 6 6 6 6 2 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 Acetic acids, substituted (CH 3)3N (CH 3)2NH CH 3NH2 CH C 6H5SO22 HO2C C 6H5SO2 F2 Br2 Cl21 F21 Br30 Cl30 F30 (2) HONC4 3 N33 I3 C 6H5O3 C 2H5O2C3 C CH 3O3 NCS3 CH C 2H5O3 3H7O 3 4H9O 3 CH C 6H5CH C (C C CH Indicates thermodynamic values. 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 Unsaturated acids Compound 2H 2H C 2CH 2CO2H 2H 3OC6H4CH 2CH 2CO2H pK ref. 20 2 2 2 2 2H 6H4CH 2CH 2CO2H Compound 2CH 2CO2H 2H C 6H5CH 2CH 2CO2H C C 6H5CH 2CH 2CO2H C 2 2 pK 4 ref. 2 2 2 2 2 2 2 Unsaturated acids, and H R2 R1 C C R1 R1 R2 R2 C C CO 2H CH ClH3 C ClC 6H4 H3 6H4 H4 CH 3CH 34 C 3)3C C 6H5CH Dicarboxylic acids, Maleic 1, 6 2 Citraconic (Dimethylmaleic acid) 2, 6 2 Acetylenedicarboxylic 1, 4 2 1 3, 5 2 Bromomaleic 1, 4 2 Bromofumaric 1, 3 2 Chlorofumaric 1, 3 2 Fumaric 3, 4 2 Mesaconic (Dimethylfumaric acid) 3, 4 2 Phthalic 2, 5 2 Itaconic acid) 3, 5 2 Chloromaleic 1, 3 2 H CO 2H Ref. 3 4 4 5 2 2 2 2 2 2 2 2 2 2 Alicyclic Dicarboxylic acids acid 2 2 2 2 acetone Lysergic acid ergometrinine isolysergic acid 7, 3 8, 3 7, 3 8, 3 2 2 2 2 2 2 2 Hydroxycyclohexanecarboxylic acids Cyclohexanecarboxylic 4 4 4 4 4 4 4 2 2 2 2 2 2 2 Aromatic 2 2 2 2 2 3 3 4 3 C 6H5OCH 3(CH 3)2CH(CH F3CHOICl(CH 3)3SiC 5H11OC 6H5CH 3CH 2(CH Substituted benzoic acids (ref. 2) o m CH 3COCH CH CH Benzene Polycarboxylic acids 1 3 3 3 3 3 3 4 8 4 4 4 4 5 5 4 5 3 3 3 4 4 5 4 4 5 for complex chelating agents, see also ref. 84. see also page 9a for more carboxylic acids. COOH Benzoic acid p benzoic acids Benzoic acid pK Ref. 2 4H93 2 3)23 2 3)44 2 3)43 2 2H53 2 2 3)33 2 3)44 2 3 Ref. 2 Acid Position of carboxyl pKI pKII Benzoic Phthalic Isophthalic Terephthalic Hemimellitic Trimellitic 1 1,2 1,3 1,4 1,2,3 1,2,4 pKIV pKV pKVI 8 Trimesic Mellophanic Prehnitic Pyromellitic Benzenepentacarboxylic Mellitic strength 0 1,3,5 1,2,3,4 1,2,3,5 1,2,4,5 1,2,3,4,5 1,3,4,5,6 Carboxylic Acids Ref. 77 Aminomalonic 3, 9 acid 2, 10 acid 2, 3, 9 3, 9 1, 8, 10 phosphonic acid 2, 2, 5, 10 2, 3, 9, 11 5, 11 3 2, 8 2, 9 Iminodipropionic 4, 9 4 Mandelic acid 3 8, 10 Methyliminodiacetic 2, 10 2, 8 2, 8 oxalic 1, 4 2, 10 1, 2, 8 acid 2 acid 2, 6 Cyanomethyliminodiacetic 3, 4 acid 1, 6 Diethylaminoacetic 2, 10 Dimethylaminoacetic 2, 9 2, 10 3 4 3 2, 9 4 2, 10 3 2, 10 Nitrilotriacetic 3, 3, 10. 1, 2, 6, 10 ALCOHOLS and other OXYGEN ACIDS Alcohols Compound pK Ref. Choline 13 6 Chloral hydrate 9, 11 61 Trifluoroethanol 12 CF3 CH2 OH 11, 12 63 CF3 CH(OH)CH3 11 63 CF3 CH2 (CH3 )3OH 12 10 C3 F7 CH2 OH 63 (C3 F7 )2 CHOH 63 OH 13 64 C(CH2 OH))4 14 64 HOCH2 CHOHCH2 OH 4 64 HOCH2 CH2 OH 14 64 CH3 CCH2 OH 14 64 CH3 OH 15 CH2 OH 15 H2 O 15 64 CH3 CH2 OH 16 64 Substituent effects for ionization of RCH2OH R 12,11 64,65 CF312 64 CHF2 CH2 12 64 CHCl2 12 64 CHEC13 64 H2 Cl14 64 CH3 CCH2 14 64 HOCH2 15 H15 64 CH2 64 CH3 (15) 64 CF3 C(CH3 )2 OH 11 64 HOCH2 CF2 CH2 OH 11 64 Primary and Secondary alcohols in alcohol C2 F5 11 65 C4 F9 11 65 C5 F11 11 65 C7 F15 11 65 CHF2 12 65 CF2 Cl 11 65 CHF2 CF2 11 65 CHF2 (CF2 )2 11 65 CF3 CH2 12 65 CF3 (CH2 )2 12 65 CF3 CHMe OH 11 65 C3 F7 CHMe OH 11 65 C3 F7 CHEt OH 11 65 C3 F7 CHPr OH 11 65 C3 F7 CH(CF3 ) OH 10 65 Compound pK C3 F7 F5) 10 (C3 F7 )2 10 62 Carbonium ions Triphenylmethanols in H 2SO 4 4 Unsubstituted triphenylmethanol6 64 4 CH2 OH CF3 CH2 OH Hydroxamic acids FuroGlycine HippuroisoNicotin 64 Other oxygen acids Dimethylglyoxime dioxane) ether Tropolone Acetald hydrate Formald hydrate a dioxane aquaeous ethanol Ref. 65 65 HC1O 4 HNO3 .82. .82 5 ref .80 66 66 66 66 66 66 8 9 8 7 8 7 6 8 8 7 7 6 66 66 72 72 72 72 8 8 72 72 72 72 72 9 4 72 72 72 18 12 12 12a 6 a 13 13 66 77 77 77 77 91 91 OTHER OXYGEN ACIDS Compound pK Ref. Pyridine oxides 3 67 3 67 3 67 perchlorate 67 2 67 perchlorate 12 67 2 67 2 67 2 67 67 1 67 3 67 perchlorate 67 2 67 2 67 67 1 67 2 67 1 67 67 Pyridine R 3 3 4 H pK 1 1 1 0 1 0 0 Peroxides ROOH (Ref. 70) H CH 3 11 11 Ref. 47 47 47 47 47 47 47 47 47 C 2H5 11 Oximes benzoquinoline methiodide Hydroxamic acids Aceto9 7, 6 Salicylo 7 Benzo8 Propiono9 Oximes Benzophenone oxime 11 18 Diethyl ketoxime 12 18 Isonitrosoacetylacetone (INAA) 7 76 8 76 Acetophenone oxime 11 18 Acetoxime 11 18 Isonitrosoacetone (INA) 8 76 Salicyclaldoxime (SA) 9 76 8 76 8 76 Oxygen acids sulfinic acids 7 1 73 73 1 1 1, 2 Peroxyacids Peroxymonosulfuric 9 Acetic 8 8 Formic 7 Propionic 8 peroxydiphosphoric 5, 7 peroxymonophosphoric 4 3H7 12 ref. 93 6 68 68 68 68 71, 72 68 68 68 68 68 12 73 73 73 73 69 70 70 70 70 85 90 4H9 12 heptiodide methiodide pentiodide 8 8 8 dine Diglycylcystine Glutathione 9 6 2 2 3 3 7 8 6 6 (L,L) Compound (L) or (D) 3 8 (L) or (D) 3 8 (LL) 3 8 (LD) 3 8 (DD) 3 8 (LD) 3 8 (3L) 3 8 (LLD) 3 8 (LDL) 3 8 (DLL) 3 8 (3D) 3 8 (4L) 3 7 (LLDL) 3 7 (LDLL) 3 7 3 7 (LL) 3 7 10 (LD) 3 7 10 (3L) 3 7 10 (LDL) 3 7 10 (LLD) 3 7 10 (4L) 3 8 10 (LDLL) 3 8 10 (5L) 3 7 10 3 7 10 (LL) 3 7 10 (LD) 2 7 9 (3L) 3 7 9 (LDL) 2 7 9 (LDD) 2 7 9 Compound pK ref. Glutathione 3, 8, 9 77 Glycylserine 8 77 Glycylleucine 8 77 Leucylglycine 7 77 Glycylisoleucine 7 77 Leucylglycylglycine 7 77 Glycylphenylalanine 8 77 Glycyltyrosine 8 77 Benzylglutamic acid 3, 4 77 Glycyltryptophane 8 77 Glutathione, oxidized 3, 4, 8, 9 77 Alanylalanine (LL) 3 8 92 Alanylalanine (LD) 3 8 92 Lysylalanine (LL) 3 7 10 92 Lysylalanine (LD) 3 7 10 92 Leucyltyrosine (LL) 3 7 10 92 Leucyltyrosine (DL) 3 8 10 92 3 3 10 11 10 10 10 10 7 7 11 23 6 Ref. 27 27 27 27 27 27 27 27 27 27 27 27 27 27 27 27 27 27 27 27 27 27 27 27 27 27 11 27 11 27 11 27 Lysyllysine (LD) 2 7 NITROGEN COMPOUNDS Aliphatic Amines pK ref. Ammonia 9 1 Primary Amines ester 9 1 Allylamine9 2 Benzyl 9 1 1 1 Cyclohexylmethyl10 1 Ethanol9 1 Ethylenedi9, 7 1, 77 Hydrazine 8 1 Isopropyl10 1 Methyl10 1 Phenylamyl10 2 1 X XNH 3 C X X(CH X(CH X(CH X(CH X(CH X(CH X(CH XCH 2 NH 3 7 7 9 10 10 10 10 10 10 10 Secondary amines 92 Trimethylsilymethyl10 CH 3ONH2 4 Allyl9 acid ester 9 Cyclohexyl10 Ethyl 10 Glycine ester 7 Hydroxyl5 Methoxy4 10 1 1 12 1 1 1 1 1 1 1 1 1 1 2 1 ? X(CH2 )2 NH 3 X(CH2 )3 NH 3 X(CH2 )4 NH 3 ref. X(CH2 )5 NH 3 2 9 9 10 2 2 2 10 10 10 10 11 2 9 10 10 10 1 5 9 10 10 11 10 11 10 9 9 10 8 10 11 11 11 7 7 10 10 5 10 9 1 1 1 1 2 2 2 2 12 1 Diisobutyl10 7 10 10 10 4 Acetanilide value 2 1 1 2 2 2 2 2 12 4

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Module: Careers and Employability for Economists (ECON1032)

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*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 (DMSO)(DMSO)pKapKa (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

-CO2H

trans

-CO2H

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

1.92, 6.23

-12.4

-7.8

-6.2

-3.8

-2.05

-2.2

-2.6

2.1

-1.8

-6.5

1.68

2.66

2.86

3.12

4.76

4.2

-O2NC6H4

-(CH3)3N+C6H4

-OMeC6H4

-ClC6H4

2.17

2.45

3.44

2.94

3.83

3.99

1.37

-(CH3)3N+C6H43.43

4.47

4.25

3.02, 4.38

Substrate Substrate

(13.7)

(18.5)

PROTONATED SPECIESCARBOXYLIC ACIDS

(31.2)

(27.9)

(29.3)

(23.5)

(18.2)

(29.4)

10.2

7.1

8.4

-OMeC6H4OH

-O2NC6H4OH

9.95 (18.0)

2-napthol (17.1)

(10.8)

(19.1)

ALCOHOLS

16.5

17.0

-hex3COH 24.0

OXIMES & HYDROXAMIC ACIDS

8.88

11.3 (20.1)

pKa

OHR

PhPh

NOH

Ph OH N+

O+

HMe

NOH

OHX

Me O+

N+

OHPh

Ph CH3

O+

Me SOH

O O

Ph SOH

MeMe

O+

MePh

For a comprehensive compilation of Bordwell pKa data see: http://www.chem.wisc.edu/areas/reich/pkatable/index.htm

H2OH2OH2O

CH3CO3H

MeOOH

CF3SO3H

(CF3)2CHOH

CF3CH2OH

-BuOH

MeOH

HOH

CF3

CCl3

CHCl2

HOOH

H2SO4

H2SO3

HSCN

H3PO4

H2S

H3O+

H2O

HNO3

HNO2

HN3

NH4Cl

H2CrO4

HCN

CH3SO3H

HClO4

HOCl

HCl

HBr

B(OH)3

CH2NO2

CH2F

CH2Cl

CH2Br

CH2I

CH3

C6H5

-PrOH

C6H5OH

(NH)

H2O

9.3

(+5.55)

NOHMe

(+1.63)

pKa Table.1 11/4/05 1:43 PM