evans_pKa_table.pdf

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1、pKa'sofInorganicandOxo-AcidsChem206SubstratepKaH2O(DMSO)SubstratepKaH2O(DMSO)SubstratepKaH2O(DMSO)SubstratepKaH2O(DMSO)INORGANICACIDSCARBOXYLICACIDSALCOHOLSPROTONATEDSPECIESH2O15.7(32)O(31.2)OHOH15.7N+-12.4H3O+-1.7XOHMeOH15.5(27.9)PhOHX=CH34.76(12.3)i-P

2、rOH(29.3)+OHH2S7.0016.5CH2NO21.68t-BuOH(29.4)-7.817.0PhOHHBr-9.00(0.9)CH2F2.66+c-hex3COH24.0OHHCl-8.0(1.8)CH2Cl2.86-6.2CH2Br2.86CF3CH2OH12.5(23.5)PhCH3HF3.17(15)CH2I3.12(CF3)2CHOH9.3(18.2)HHOCl7.5CHCl21.29O+-6.5C6H5OH9.95(18.0)PhMeHClO4-10CCl30.65HCF-0.

3、25m-O2NC6H4OH8.43O+-3.8HCN9.4(12.9)H3.77p-O2NC6H4OH7.1(10.8)MeMeHN34.72(7.9)HO3.6,10.3p-OMeC6H4OH10.2(19.1)+OH-2.05C6H54.2(11.1)2-napthol(17.1)HHSCN4.00o-O2NC6H42.17O+-2.2H2SO31.9,7.21m-ONCH2.45OXIMES&HYDROXAMICACIDSMeH264+OH-3.0,1.99p-O2NC6H43.44OH-1.8

4、H2SO4NSo-ClCH2.9411.3(20.1)MeMe64H3PO42.12,7.21,PhPh12.32m-ClC6H43.83O(13.7)N+OH0.79(+1.63)HNO3-1.3p-ClCH3.99OH8.8864PhN(NH)HNO3.29+1.37OHMe2o-(CH3)3NC6H4+OH(18.5)MeNOH(+5.55)HCrO-0.98,6.50p-(CH3)3NC6H43.43PhNMe24p-OMeC6H44.47MeCH3SO3H-2.6(1.6)SULFINIC&

5、SULFONICACIDSOPEROXIDESCF3SO3H-14(0.3)ROHOONH4Cl9.24S-2.6R=H4.25MeOOH11.5MeOHB(OH)39.23trans-CO2H3.02,4.388.2OCH3CO3H2.1HOOH11.6cis-COH1.92,6.23S2PhOH*Values<0forH2OandDMSO,andvalues>14forwaterand>35forDMSOwereextrapolatedusingvariousmethods.Foracompreh

6、ensivecompilationofBordwellpKadatasee:http://www.chem.wisc.edu/areas/reich/pkatable/index.htmpKaTable.111/4/051:43PMD.H.Ripin,D.A.EvanspKa'sofNitrogenAcidsChem206SubstratepKaH2O(DMSO)SubstratepKaH2O(DMSO)SubstratepKaH2O(DMSO)SubstratepKaH2O(DMSO)PROTONA

7、TEDNITROGENAMINESIMIDESHYDROXAMICACID&AMIDINESN+H9.2(10.5)HN34.7(7.9)OOO48.88(13.7)EtN+H10.6NH338(41)OH(NH)3NH8.30NH(14.7)PhNi-Pr2NH(36THF))Hi-Pr2N+H211.05NSOPhTMS2NH26(THF)(30)2R=Me(17.3)OOEt3N+H10.75(9.00)PhNH(30.6)AcNH(17.9)Ph(15.0)22RNH2PhN+H34.6(3.

8、6)PhNH(25.0)Me2MeSULFONAMIDEPhN+(Me)2H5.20(2.50)NCNH2(16.9)HETEROCYCLESNH(37)RSO2NH2R=Me(17.5)Ph2N+H20.78NH(44)Ph(16.1)H(20.95)HMeCF6.3(9.7)NN(16.4)2-napthal-N+H4.16Me33MeSO2NHPh(12.9)H2NN+H38.12H2NN(26.5)HNGUANIDINIUM,(11.9)NHON