LectureSupplement:pKaValuesofSelectedCompounds15pKaValuesofSelectedCompounds•Instructureswithmorethanoneprotontype,protoncorrespondingtogivenpKaisinbold.•ValuesinparenthesesarealternatepKavaluesgivenbysomesources.Inorganic(Mineral)AcidsHSbF6-12HClO4-10HI-10H2SO4pKa1=-9(-5);pKa2=2.0HBr-9(-5.8)HCl-7(-3.9)HNO3-1.3H3PO4pKa1=2.1;pKa2=7.2;pKa3=12.3HF3.2H2O15.7OxoniumIons(R3O+)HHOHOOCH3HOOHHO-8-7.3-6.5-6.1(CH3)2OH(CH3CH2)2OHCH3OH2CH3CH2OH2-3.8-3.6-2.5-2.4H3ONH2HO-1.70.0CarboxylicAcids(RCO2H)CF3CO2HCl3CCO2HHO2C-CO2HCl2CHCO2H0.20.64pKa1=1.2;pKa2=4.21.3CO2HCO2HH3NCO2HFCH2CO2HClCH2CO2HpKa1=1.9;pKa2=6.12.22.72.816LectureSupplement:pKaValuesofSelectedCompoundsCO2HClCO2HOHBrCH2CO2HCO2HCO2H2.832.92.9pKa1=2.9;pKa2=5.4HO2CH2CO2HHO2CCO2HICH2CO2HCO2HO2NpKa1=2.9;pKa2=5.7pKa1=3.0;pKa2=4.43.23.4OOCH3CO2HCO2HHO2CCO2HHO2CHCO2H3.5pKa1=3.5;pKa2=4.6pKa1=3.5;pKa2=4.83.7ClCH2CH2CO2HCO2HBrCO2HHO2C(CH2)2CO2H3.984.04.2pKa1=4.2;pKa2=5.6HO2C(CH2)3CO2HCO2HH3CCO2HH3COCH3CO2HpKa1=4.3;pKa2=5.44.34.54.78CH3(CH2)8CO2HCH3(CH2)6CO2HCH3(CH2)14CO2HH2CO34.844.896.5pKa1=6.5;pKa2=10.2Phenols(ArOH)OHNO2NO2O2NOHNO2O2NOHNO2OHO2N0.784.07.27.2OHClOHO2NOHClOHCl8.18.38.89.3LectureSupplement:pKaValuesofSelectedCompounds17OHOHOHOHH3C9.39.610.010.1OHH3COHCH3OHH2N10.210.210.3Aminium(R3NH+)andIminium(R2C=NH+)IonsNHHO2NNH3BrNH3ClNH30.801.03.94.0NH3NHHCH3NHNHCH3CH34.64.74.95.06H3CNH3NHH3CONH3NHH3C5.15.25.35.5HONH3HNNHH3NCO2CH3NH26.06.87.758.0H2NNH3ONH2CH2NH3NH48.19.39.39.4HOCH2CH2NH3O2CCH2NH3(CH3)3NHNH39.59.79.810.4518LectureSupplement:pKaValuesofSelectedCompoundsNH3NH3NH3(CH3CH2CH2)3NH10.4910.5610.6110.64CH3NH3NH3NH3NH310.6510.6710.6710.73CH3CH2NH3(CH3CH2)2NH2(CH3CH2CH2)2NH2NH210.7610.9810.9811.15NH211.2Alcohols(ROH)OOHOCF3CH2OHHCCCH2OH(CH3)3NCH2CH2OH8.212.413.513.9CH3OHH2OCH3CH2OHOH15.515.716-1717OHOH1818-19CarbonylCompounds:α-DeprotonationtoFormEnolateHOOHHOOHHOCH2CH3OOHHCH3CH2OOCH2CH3OOHH5.99.011.013.3LectureSupplement:pKaValuesofSelectedCompounds19HOHPhCH3OH3CHOH3CCH3O15.515.91719-20OCH3HHOH3COCH2CH3OH3CN(CH3)2O2223-24.530Amides(O=C-N-H)NHOONH2O915-16Amines(R2N-H)NNNHNNHNNHNH8.914.41736NHNH3CH3NH23636-3840SulfurandSeleniumCompoundsF3CSOOOHSOOOHCH3SH2H3CSOOOH-16-6.5to–0.6-6.8-1.2H2SeH2SSHCH3CH2SH3.897.07.810.5CH3SHSSHHSH3CCH3O10.73131.320LectureSupplement:pKaValuesofSelectedCompoundsHydrocarbons(R3C-H)HHHHHHCCHH15–16202325-26Ph3CHH2CCH2CH33336-4539-4641H2CCHCH3CH4CH3CH3434349-6050-62MiscellaneousCompoundsNHHHNOOCH3CH2CNHNOOH3C-3.88.69.110.2CNH3CCHCl3H2252535