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Table 3.17 THE EFFECT OF  PHENYL SUBSTITUTION
                                                       ON
                        SOLUTION BASICITY OF  OXYGEN AND  NITROGEN BASES
               Compound                   PKU









              a E.  M. Arnett, R. P.  Quirk, and J. W. Larsen, J. Amer. Chem. SOC., 92,  1260 (1970).
                See Table 3.2.
                D.  D.  Perrin, Dissociation Constants of  Organic Bases  in Aqueous  Solution,  Butterworths,  London,  1965.
                Estimated from data of Arnett et  al.,  (note a).




               Table 3.18 GAS-PIIASE BASICITIES SELECTED COMPOUNDS
                                          OF
               Compound                        Proton Affinitya
                                               (kcal mole- l)
               CH4                                 127             Increasing basicity
               H2C=CH2                             159
               CH3Cl                               164                               \
               Hz0                                 165
               H2S                                 170
               HCOOH                               177
               CH3-CH=CH2                          182
               CH30H                               182
               CH3SH                               185b
               pH3                                 185,b 188'
               CH3COOH
               CH3CH20H
               CH3-0-CH3
               (CH3),CHOH
               CH3COCH3
               CH3-S-CH3
               (CH3)3COH
               CH3CH2-0-CH2CH3
               NH3
               CH3PH2
               4NH2                                216b
                                                   d
               42NH
               CH3NH2                              216b
               43N                                 d
               (CH3)2PH                            219'
               (CH3)zNH                            2228
               (CH3)3N                             227b
               (CH3)3P                             228'          Decreasing basicity
               a  Except  where noted,  data arE from the compilation of J. Long and  B.  Munson,  J. Amer.  Chem.
               Sod.,  95, 2427  (1973).
                E.  M. Arnett, Accts.  Chem. Res.,  6, 404  (1973).
                R. H. Staley and J. L. Beauchamp, J. Amer. Chem. Sod., 96,6252 (1974).
                I. Dzidic, J. Amer. Chem. Soc., 94,8333 (1972). Only relative basicities reported for these compounds.
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