pka's of Inorganic and Oxo-Acids
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1 's of Inorganic and xo-acids ubstrate Br Cl F Cl Cl 4 C 3 C P Cr 4 C Cl B() 3 IRGAIC ACID Table.1 11/4/05 1:43 PM (DM) (32) (0.9) (1.8) (15) 1.9, 7.21 (12.9) (7.9) -3.0, , 7.21, , (1.6) (0.3) ubstrate = C 3 C 2 2 C 2 F C 2 Cl C 2 Br R cis-c 2 CARBYLIC ACID C 2 I CCl 2 CCl 3 C 6 5 o- 2 C 6 4 m- 2 C 6 4 p- 2 C 6 4 o-clc 6 4 m-clc 6 4 R= trans-c 2 2 (DM) 4.76 (12.3) p-clc o-(c 3 ) 3 C p-(c 3 ) 3 C p-c , (11.1) , , 6.23 ubstrate t-bu m- 2 C 6 4 p- 2 C 6 4 p-c 6 4 ALCL PERIDE *Values <0 for 2 and DM, and values >14 for water and >35 for DM were extrapolated using various methods c-hex 3 C 24.0 C 2 ( ) 2 C C (DM) (31.2) (27.9) (29.3) (29.4) (23.5) 9.95 (18.0) (10.8) (19.1) 2-napthol (17.1) IME & YDRAMIC ACID C 3 C (20.1) 8.88 (13.7) () (18.5) ubstrate PRTATED PECIE C (DM) ULFIIC & ULFIC ACID For a comprehensive compilation of Bordwell data see: (1.63) (5.55)
2 D.. Ripin, D.A. Evans 's of itrogen Acids ubstrate 2 (DM) ubstrate 2 (DM) ubstrate 2 (DM) ubstrate 2 (DM) PRTATED ITRGE 9.2 (10.5) TM (9.00) (3.6) 2 2 (30.6) (25.0) () (2.50) C DABC napthal Quinuclidine 11.0 (9.80) Morpholine morpholine Proton ponge C , 8.82 (2.97, 8.93) 6.90, (44) AMIE R= 4.7 (7.9) 38 (41) (36 TF)) 26(TF) (30) (26.5) C 3 (urea) 2 (21.6) 15.1 (37) AMIDE & CARBAMATE R 2 n= 1 (24.1) n= 2 (26.4) ( ) n (23.5) (25.5) (23.3) (26.9) (24.8) 12 (20.5) Bn DMAP (12) (estimate) -9.0, 12.0 R R= 5.21 (3.4) (--, 7.50) (15) (PPT) t-bu 4.95 (0.90) (12.1) 6.75 (4.46) (18.4) -10 R Cl, 0.72 *Values <0 for 2 and DM, and values >14 for water and >35 for DM were extrapolated using various methods. IMIDE 8.30 ULFAMIDE 9.2 (14.7) (17.9) (13.6) 2 (21.6) (18.9) (17.5) (16.1) 6.3 (9.7) (12.9) GUAIDIIUM, YRDAZE,- IDE, & -IE (26.1) PRTATED ETERCYCLE R 2 2 (20.95) 8.88 (13.7) () R= (17.3) (15.0) ETERCYCLE For a comprehensive compilation of Bordwell data see: Table.2 11/4/05 1:43 PM Ac 2 R 2 2 R = DBU YDRAMIC ACID & AMIDIE (19.8) (11.9) = (24) = (13.3) = (14.8) = (11.8) (23.0) (16.4) (13.9) = (24.4) = (27.0) (29.4) (16.5) (24)
3 D.. Ripin, D.A. Evans 's of C bonds in ydrocarbons and Carbonyl Compounds ubstrate 2 (DM) ubstrate 2 (DM) ubstrate 2 (DM) ubstrate 2 (DM) () 3 C () 2 C 2 C 2 =C 2 C 4 C 2 =CC 3 C 3 2 C 2 3 C CC CC C 6 4 C 3 = p-c 2 YDRCARB p- 2 p-c Table.3 11/4/05 1:44 PM ~36 (56) (44) (43) (32.2) (30.6) 23 (28.8) (30.8) (20.4) (26.9) (26.1) (20.1) (18.0) t-bu t-bu Li ETER 3 AMIDE 3 C (30.3) (23.6) (20.0) (14.2) (15.7) (20.9) [30.2 (TF)] (26.6) (25.9) (25.7) (27.1) *Values <0 for 2 and DM, and values >14 for water and >35 for DM were extrapolated using various methods. = = CC 3 2 t-bu C 3 CC 3 C C F e KETE (26.5) (19.8) (18.7) (13.3) (12.5) (28.3) (27.7) (26.3) (24.7) (24.4) (17.7) (14.2) (13.3) (10.2) (21.6) (22.85) (21.1) (20.3) (14.6) (7.7) (11.4) = n n= 2 Br C For a comprehensive compilation of Bordwell data see: (24.7) (25.7) (27.5) (23.8) (22.0) (25.1) (25.8) (26.4) (27.7) (27.4) (28.1) (29.0) (25.5) (32.4)
4 D.. Ripin, D.A. Evans 's of C bonds at itrile, eteroaromatic, and ulfur ubstituted Carbon ubstrate 2 (DM) ubstrate 2 (DM) ubstrate 2 (DM) ubstrate 2 (DM) C = - C 3 C CR 2 C 2 C 3 2 ITRILE 11 ETER-ARMATIC (31.3) (32.5) (21.9) (10.2) (17.1) (13.1) (11.1) (28.1) (20.6) (12.0) (28.2) (30.1) (26.7) (25.2) (30.2) (30.0) C 2 = C CC 3 C P 2 C 2 2 C 2 () 3 C (Pr) 3 C () 2 C = C 2 C RC 2 C R= t-bu ULFIDE (30.8) (18.7) (11.8) (30.8) (20.5) (11.0) (23.4) (26.7) (22.8) (31.3) (30.5) (23.0) (30.7) (19.1) (24.3) (24.0) (23.6) (22.9) C=CC 2 (26.3) Bu (17.0)!7 (10.3) = (35.1) (29.0) (29.0) ULFIUM *Values <0 for 2 and DM, and values >14 for water and >35 for DM were extrapolated using various methods. = R= C 2 3 = ULFIDE (33) (27.2) (24.5) (16.3) ULFIMIDE & ULFIMIE Ts R Ts 2 Ts C 2 C 2 Cl (27.6) (30.7) (24.5) (33) (14.4) (20.7) = C 3 t-bu C=C 2 C=C CC CC C C 3 C 2 2 P 2 ULFE C 2 ( 2 ) 2 C 2 (29.0) (31.0) (31.2) (23.4) (22.5) (20.2) (22.1) (17.8) (11.4) (12.5) (27.9) (19.4) (12.0) (7.1) (23.5) (20.5) (12.2) (20.2) (22.3) (31.1) (18.8) (21.8) (26.6) (32.8) (14.3) Table.4 11/4/05 1:44 PM
5 D.. Ripin, D. A. Evans 's of C bonds at eteroatom ubstituted Carbon & References ubstrate 2 (DM) ubstrate 2 (DM) ubstrate C 3 C 2 2 C 2 2 C 2 C e = 2 C C 2 ec 2 (e) 2 C 2 ec 2 C 2 ELEIDE ETER ec=cc 2 e 3 C 2 C AMMIUM (49) (30.7) (27.9) (28.1) (22.85) (27.5) (31.3) (31.0) (27.2) (20.6) (19.4) (14.6) (20.0) P 4 P 3 3 P 3 P C 3 3 P 3 P C 2 C () 2 P = = 2 P PPATE & PPIE IDE C C 2 Cl i 3 C 2 PC 2 P 2 PPIUM 3 P C 2 C 2 PC 2 2 PPIE (22.4) (21.2) (6.2) (7.0) (27.6) (16.4) (26.2) (28.8) (29.9) (20.2) R 2 R= 2 n= C 3 C 2 C 2 C 2 C 2 Bn C 2 C 2 2 C 2 C n ITR IMIE 2!10 (DM) (16.7) (12.2) (16.2) (11.8) (7.1) (7.7) (26.9) (17.8) (16.0) (17.9) (15.8) (24.3) xime ethers are ~ 10 pka units less acidic than their ketone counterparts treitwieser, JC 1991, 56, 1989 DM: REFERECE JAC 97, 7007 (1975) JAC 97, 7160 (1975) JAC 97, 442 (1975) JAC 105, 6188 (1983) JC 41, 1883 (1976) JC 41, 1885 (1976) JC 41, 2786 (1976) JC 41, 2508 (1976) JC 42, 1817 (1977) JC 42, 321 (1977) JC 42, 326 (1977) JC 43, 3113 (1978) JC 43, 3095 (1978) JC 43, 1764 (1978) JC 45, 3325 (1980) JC 45, 3305 (1980) JC 45, 3884 (1980) JC 46, 4327 (1981) JC 46, 632 (1981) JC 47, 3224 (1982) JC 47, 2504 (1982) Acc. Chem. Res. 21, 456 (1988) Unpublished results of F. Bordwell Water: Advanced rg. Chem., 3rd Ed. J. March (1985) Unpublished results of W. P. Jencks TF: JAC 110, 5705 (1988) ee cited website below for additional data *Values <0 for 2 and DM, and values >14 for water and >35 for DM were extrapolated using various methods. For a comprehensive compilation of Brodwell data see: Table.5 11/4/05 1:45 PM
6 DM Acidities of Common eterocycles Bordwell, ACR, 1988, 21, 456 Bordwell Pka Table.6.cdx 11/4/05 1:45 PM
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