Evans 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) pKa Table.1 11/4/05 1:43 PM
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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 (12) (estimate) pKa's of Nitrogen Acids (DMSO) Chem 206 Substrate Substrate Substrate pKa Substrate DABCO (41) (36 THF)) (37) (30) (10.5) 9.2 10.6 11.05 10.75 (30.6) (25.0) 4.6 0.78 2-napthal-N + H 3 4.16 (3.6) 8.12 5.96 + -9.3
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This note was uploaded on 11/19/2010 for the course LECTURE 1 taught by Professor Yildiz during the Fall '10 term at University of California, Berkeley.

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Evans pKa Table - pKa's of Inorganic and Oxo-Acids...

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