preface to fifteenth edition

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9.2 SECTION 9 9.1 LINEAR FREE ENERGY RELATIONSHIPS Many equilibrium and rate processes can be systematized when the influence of each substituent on the reactivity of substrates is assigned a characteristic constant and the reaction parameter is known or can be calculated. The Hammett equation K log K describes the behavior of many meta- and para-substituted aromatic species. In this equation K is the acid dissociation constant of the reference in aqueous solution at 25C and K is the corresponding constant for the substituted acid. Separate sigma values are defined by this reaction for meta and para substituents and provide a measure of the total electronic influence (polar, inductive, and resonance effects) in the absence of conjugation effects. Sigma constants are not valid of substituents ortho to the reaction center because of anomalous (mainly steric) effects. The inductive effect is transmitted about equally to the meta and para positions. Consequently, m is an approximate measure of the size of the inductive effect of a given substituent and p m is an approximate measure of a substituent’s resonance effect. Values of Hammett sigma constants are listed in Table 9.1. Taft sigma values * perform a similar function with respect to aliphatic and alicyclic systems. Values of * are listed in Table 9.1. The reaction parameter depends upon the reaction series but not upon the substituents employed. Values of the reaction parameter for some aromatic and aliphatic systems are given in Tables 9.2 and 9.3. Since substituent effects in aliphatic systems and in meta positions in aromatic systems are essentially inductive in character, * and m values are often related by the expression m 0.217* 0.106. Substituent effects fall off with increasing distance from the reaction center; generally a factor of 0.36 corresponds to the interposition of a 9CH 2 9 group, which enables * values to be estimated for R9CH 2 9 groups not otherwise available. TABLE 9.1 Hammett and Taft Substituent Constants Substituent Taft Hammett constants m p * constant 9AsO H 3 0.09 0.02 0.06 9B(OH) 2 0.01 0.45 9Br 0.39 0.23 2.84 9CH 2 Br 1.00 m-BrC 6 H 4 9 0.09 p-BrC 6 H 4 9 0.08 9CH 3 0.07 0.17 0.0 9CH 2 CH 3 0.07 0.15 0.10 9CH 2 CH 2 CH 3 0.05 0.15 0.12 9CH(CH 3 ) 2 0.07 0.15 0.19 9CH 2 CH 2 CH 2 CH 3 0.07 0.16 0.13 9CH 2 CH(CH 3 ) 2 0.07 0.12 0.13 9CH(CH 3 )CH 2 CH 3 0.12 0.19 9C(CH 3 ) 3 0.10 0.20 0.30 9CH 2 CH 2 CH 2 CH 2 CH 3 0.25 9CH 2 CH 2 CH(CH 3 ) 2 0.17
PHYSICOCHEMICAL RELATIONSHIPS 9.3 TABLE 9.1 Hammett and Taft Substituent Constants (Continued) Substituent Taft Hammett constants m p * constant 9CH 2 C(CH 3 ) 3 0.23 0.12 9CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 0.37 Cyclopropyl9 0.07 0.21 Cyclohexyl9 0.15 93,4-(CH 2 ) 2 (fused) 0.26 93,4-(CH 2 ) 3 9 (fused ring) 0.48 93,4-(CH) 4 9 (fused ring) 0.06 0.04 9CH"CH 2 0.02 0.56 9CH"C(CH 3 ) 2 0.19 9CH"CHCH 3 , trans 0.36 9CH 2 9CH"CH 2 0.0 9CH"CHC 6 H 5 0.14 0.05 0.41 9C#CH 0.21 0.23 2.18 9C#CC 6 H 5 0.14 0.16 1.35 9CH 2 9C#CH 0.81 9C 6 H 5 0.06 0.01 0.60 p-CH 3 C 6 H 4 9 0.5 Naphthyl9 (both 1- and 2-) 0.75 9CH 2 C 6 H 5 0.46 0.22 9CH 2 CH 2 9C 6 H 5 0.06 9CH(CH 3 )C 6 H 5 0.37 9CH(C 6 H 5 ) 2 0.41 9CH 2 9C 10 H 7 0.44 2-Furoyl9 0.25 3-Indolyl9 0.06 2-Thienyl9 1.31 2-Thienylmethylene9 0.31 9CHO 0.36 0.22 9COCH 3 0.38 0.50 1.65 9COCH 2 CH 2 0.48 9COCH(CH 3 ) 2 0.47 9COC(CH 3 ) 3 0.32 9COCF 3 0.65 3.7 9COC 6 H 5 0.34 0.46 2.2 9CONH 2 0.28 0.36 1.68 9CONHC 6 H 5 1.56 9CH 2 COCH 3 0.60 9CH 2 CONH 2 0.31 9CH 2 CH 2 CONH 2 0.19 9CH 2 CH 2 CH 2 CONH 2 0.12 9CH 2 CONHC 6 H 5 0.0 9COO 0.1 0.0 1.06 9COOH 0.36 0.43 2.08 9CO9OCH 3 0.32 0.39 2.00 9CO9OCH 2 CH 3 0.37 0.45 2.12 9CH 2 CO9OCH 3 1.06 9CH 2 CO9OCH 2 CH 3 0.82 9CH 2 COO 0.06 9CH 2 CH 2 COOH 0.03 0.07 9Cl 0.37 0.23 2.96 9CCl 3 0.47 2.65 9CHCl 2 1.94
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LANGE'S HANDBOOK OF CHEMISTRY John
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Grateful acknowledgment is hereby m
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PREFACE TO FIFTEENTH EDITION This n
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PREFACE TO FIFTEENTH EDITION ix inv
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xii PREFACE TO FOURTEENTH EDITION l
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PREFACE TO FIRST EDITION This book
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For the detailed contents of any se
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1.2 SECTION 1 is derived from the G
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1.4 SECTION 1 rather than methylide
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1.6 SECTION 1 Styrene Toluene Xylen
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1.8 SECTION 1 TABLE 1.2 Fused Polyc
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1.10 SECTION 1 1.1.1.6 Bridged Hydr
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1.12 SECTION 1 TABLE 1.4 Suffixes f
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1.14 SECTION 1 TABLE 1.5 Trivial Na
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1.16 SECTION 1 TABLE 1.6 Trivial Na
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1.18 SECTION 1 Selection of the pri
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1.20 SECTION 1 attached to one anot
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1.22 SECTION 1 When side chains of
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1.24 SECTION 1 heterocyclic structu
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1.26 SECTION 1 Bivalent radicals of
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1.28 SECTION 1 Complex linear polya
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1.30 SECTION 1 TABLE 1.11 Names of
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1.32 SECTION 1 hydroxyamino- to the
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1.34 SECTION 1 may be named (1) by
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1.36 SECTION 1 Examples are methyl
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1.38 SECTION 1 tuted acid, respecti
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1.40 SECTION 1 FIGURE 1.2 Newman pr
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1.42 SECTION 1 from the ring are kn
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1.44 SECTION 1 FIGURE 1.11 Two isom
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1.46 SECTION 1 Chiral Center. The c
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1.48 SECTION 1 FIGURE 1.15 Isomers
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1.50 SECTION 1 entries to bring tog
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1.52 SECTION 1 TABLE 1.13 Names and
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1.60 SECTION 1 TABLE 1.14 Empirical
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2.2 SECTION 2 2.3.6 Student’s Dis
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2.4 SECTION 2 TABLE 2.1 Fundamental
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2.6 SECTION 2 TABLE 2.1 Fundamental
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2.8 SECTION 2 TABLE 2.2 Physical an
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2.10 SECTION 2 TABLE 2.2 Physical a
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2.24 SECTION 2 TABLE 2.3 Mathematic
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2.26 SECTION 2 TABLE 2.6 Abbreviati
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2.36 SECTION 2 TABLE 2.7 Conversion
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2.54 SECTION 2 TABLE 2.8 Temperatur
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2.66 SECTION 2 2.1.1 Conversion of
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2.68 SECTION 2 Oleometer. A hydrome
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2.70 SECTION 2 Example 3. 25 1.2500
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2.72 SECTION 2 TABLE 2.9 Barometer
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2.74 SECTION 2 TABLE 2.9 Barometer
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2.76 SECTION 2 TABLE 2.10 Barometri
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2.78 SECTION 2 TABLE 2.12 Reduction
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2.80 SECTION 2 TABLE 2.12 Reduction
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2.82 SECTION 2 TABLE 2.13 Viscosity
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2.84 SECTION 2 TABLE 2.14 Conversio
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2.86 SECTION 2 TABLE 2.15 Hydromete
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2.88 SECTION 2 TABLE 2.17 Correctio
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2.90 SECTION 2 TABLE 2.18 Pressure
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2.96 SECTION 2 TABLE 2.20 Values of
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2.98 SECTION 2 TABLE 2.21 Transmitt
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2.100 SECTION 2 TABLE 2.21 Transmit
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2.102 SECTION 2 2.2 MATHEMATICAL TA
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2.104 SECTION 2 TABLE 2.23 Derivati
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2.106 SECTION 2 TABLE 2.24 Integral
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2.108 SECTION 2 TABLE 2.24 Integral
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2.110 SECTION 2 Regular Polygon of
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2.112 SECTION 2 A h[0.4(y y ) 1.
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2.114 SECTION 2 2.2.3.1 Signs of th
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2.116 SECTION 2 x2 x3 x4 x5 ln(1 x
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2.118 SECTION 2 2.3.2 Errors in Qua
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2.120 SECTION 2 The breadth or spre
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2.122 SECTION 2 TABLE 2.26b Areas U
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2.124 SECTION 2 The distribution of
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2.126 SECTION 2 Should there be mor
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2.128 SECTION 2 Example 10 Six samp
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2.130 SECTION 2 2.3.9 The F Statist
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TABLE 2.29 F Distribution (Continue
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2.134 SECTION 2 mathematical treatm
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2.136 SECTION 2 The confidence limi
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2.138 SECTION 2 situation where rel
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3.2 SECTION 3 The alphabetical orde
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3.4 SECTION 3 When it is required t
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3.6 SECTION 3 PO phosphoryl SeO sel
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3.8 SECTION 3 3.1.5 Acids 3.1.5.1 A
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3.10 SECTION 3 3.1.6.6 Multiplicati
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3.12 SECTION 3 3.2 PHYSICAL PROPERT
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TABLE 3.2 Physical Constants of Ino
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3.62 SECTION 3 TABLE 3.3 Synonyms a
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SECTION 4 PROPERTIES OF ATOMS, RADI
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4.3 Fermium Fm 100 [Rn] 5f 12 7s 2
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Silver (argentum) Ag 47 [Kr] 4d 10
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PROPERTIES OF ATOMS,RADICALS,AND BO
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PROPERTIES OF ATOMS, RADICALS, AND
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SECTION 5 PHYSICAL PROPERTIES 5.1 S
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PHYSICAL PROPERTIES 5.3 5.1 SOLUBIL
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TABLE 5.1 Solubility of Gases in Wa
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TABLE 5.1 Solubility of Gases in Wa
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TABLE 5.2 Solubilities of Inorganic
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formateBa(CHO 2 ) 2 26.2 28.0 29.9
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(III) sulfateCe 2 (SO 4 ) 3 ·9H 2
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iodidePbI 2 0.044 0.056 0.069 0.090
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Nickel sulfateNiSO 4 ·6H 2 O (pale
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Praseodymium bromatePr(BrO 3 ) 3 55
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formate NaCHO 2 43.9 62.5 81.2 102
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Uranyl nitrate UO 2 (NO 3 ) 2 98 10
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PHYSICAL PROPERTIES 5.25 TABLE 5.3
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PHYSICAL PROPERTIES 5.57 5.3 BOILIN
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TABLE 5.12 Ternary Azeotropic Mixtu
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TABLE 5.12 Ternary Azeotropic Mixtu
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PHYSICAL PROPERTIES 5.83 5.4 FREEZI
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PHYSICAL PROPERTIES 5.87 5.5 DENSIT
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PHYSICAL PROPERTIES 5.89 dt Dt P
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PHYSICAL PROPERTIES 5.135 5.6.1 Ref
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PHYSICAL PROPERTIES 5.137 where the
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PHYSICAL PROPERTIES 5.139 5.7 COMBU
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Temperature, C Substance 40 20 0 20
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PHYSICAL PROPERTIES 5.171 This equa
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SECTION 6 THERMODYNAMIC PROPERTIES
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THERMODYNAMICPROPERTIES 6.3 6.1.1.2
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THERMODYNAMICPROPERTIES 6.5 A gener
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THERMODYNAMICPROPERTIES 6.7 TABLE 6
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THERMODYNAMICPROPERTIES 6.9 TABLE 6
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THERMODYNAMICPROPERTIES 6.11 TABLE
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THERMODYNAMIC PROPERTIES 6.21 TABLE
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THERMODYNAMIC PROPERTIES 6.101 TABL
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THERMODYNAMIC PROPERTIES 6.143 The
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SECTION 7 SPECTROSCOPY 7.1 X-RAY ME
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SPECTROSCOPY 7.3 TABLE 7.1 Waveleng
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SPECTROSCOPY 7.9 TABLE 7.3 Critical
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SPECTROSCOPY 7.11 TABLE 7.4 X-Ray E
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SPECTROSCOPY 7.13 Emission line K 1
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SPECTROSCOPY 7.15 TABLE 7.7 Analyzi
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SPECTROSCOPY 7.17 TABLE 7.8 Mass Ab
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SPECTROSCOPY 7.19 TABLE 7.9 Electro
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SPECTROSCOPY 7.21 TABLE 7.11 Absorp
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SPECTROSCOPY 7.23 TABLE 7.13 Solven
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SPECTROSCOPY 7.25 7.3 FLUORESCENCE
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SPECTROSCOPY 7.27 TABLE 7.16 Fluore
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SPECTROSCOPY 7.29 TABLE 7.18 Detect
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SPECTROSCOPY 7.35 TABLE 7.19 Sensit
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SPECTROSCOPY 7.37 TABLE 7.19 Sensit
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SPECTROSCOPY 7.39 In terms of m ,
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SPECTROSCOPY 7.41 The ionization co
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SPECTROSCOPY 7.67 TABLE 7.28 Infrar
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7.69
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SPECTROSCOPY 7.71 7.6 RAMAN SPECTRO
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SPECTROSCOPY 7.73 TABLE 7.30 Raman
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SPECTROSCOPY 7.89 7.7 NUCLEAR MAGNE
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SPECTROSCOPY 7.91 TABLE 7.41 Nuclea
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SPECTROSCOPY 7.93 TABLE 7.42 Proton
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SPECTROSCOPY 7.95 TABLE 7.44 Estima
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SPECTROSCOPY 7.97 TABLE 7.46 Proton
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SPECTROSCOPY 7.99 TABLE 7.48 Solven
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SPECTROSCOPY 7.101 TABLE 7.49 Carbo
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SPECTROSCOPY 7.103 TABLE 7.51 Effec
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SPECTROSCOPY 7.107 TABLE 7.56 One-B
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SPECTROSCOPY 7.113 TABLE 7.63 Nitro
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SPECTROSCOPY 7.115 TABLE 7.64 Nitro
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SPECTROSCOPY 7.117 TABLE 7.69 Fluor
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SPECTROSCOPY 7.119 TABLE 7.72 Silic
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SPECTROSCOPY 7.121 TABLE 7.73 Phosp
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SPECTROSCOPY 7.123 TABLE 7.74 Phosp
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SPECTROSCOPY 7.125 when z 3 and y
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SPECTROSCOPY 7.127 Masses 19 and 31
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SPECTROSCOPY 7.129 TABLE 7.76 Conde
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SECTION 8 ELECTROLYTES, ELECTROMOTI
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ELECTROLYTES, EMF, AND CHEMICAL EQU
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TABLE 8.7 Proton Transfer Reactions
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TABLE 8.7 Proton Transfer Reactions
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TABLE 8.9 Selected Equilibrium Cons
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8.75 3-tert-Butylbenzoic acid (0) 4
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4-Hydroxyproline (1) 1.900 1C 1.850
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N-Propionylglycine (1) 3.728 3.723
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TABLE 8.14 National Bureau of Stand
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1 part 0.1% neutral red in alc. * V
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TABLE 10.2 Properties of Commercial
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10.58 SECTION 10 10.4 FORMULAS AND
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10.60 SECTION 10 10.4.8 Polychlorop
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10.62 SECTION 10 Styrene-butadiene
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10.5 CHEMICAL RESISTANCE TABLE 10.4
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10.6 GAS PERMEABILITY TABLE 10.5 Ga
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TABLE 10.5 Gas Permeability Constan
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TABLE 10.7 Constants ofFats and Oil
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TABLE 10.8 Constants ofWaxes Wax Me
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SECTION 11 PRACTICAL LABORATORY INF
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11.4 SECTION 11 TABLE 11.2 Molecula
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11.6 SECTION 11 A saturated aqueous
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11.8 SECTION 11 TABLE 11.6 Relative
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11.10 SECTION 11 11.3 BOILING POINT
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11.12 SECTION 11 TABLE 11.8 Organic
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11.14 SECTION 11 TABLE 11.9 Molecul
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11.4 SEPARATION METHODS TABLE 11.11
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11.18 SECTION 11 TABLE 11.12 Solven
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11.20 SECTION 11 TABLE 11.12 Solven
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TABLE 11.13 McReynolds’ Constants
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TABLE 11.13 McReynolds’ Constants
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11.26 SECTION 11 11.4.1 McReynolds
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11.28 SECTION 11 11.4.2.2 Partition
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11.30 SECTION 11 FIGURE 11.2 Band a
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11.32 SECTION 11 11.4.3 Ion-Exchang
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11.34 SECTION 11 TABLE 11.16 Guide
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11.36 SECTION 11 TABLE 11.16 Guide
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11.38 SECTION 11 TABLE 11.18 Relati
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11.40 SECTION 11 distribution coeff
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11.42 SECTION 11 TABLE 11.19 Gravim
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11.68 SECTION 11 TABLE 11.20 Elemen
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11.70 SECTION 11 TABLE 11.22 Common
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11.72 SECTION 11 TABLE 11.25 Tolera
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11.74 SECTION 11 TABLE 11.26 Heatin
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11.76 SECTION 11 TABLE 11.28 Titrim
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11.84 SECTION 11 appears becomes le
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11.86 SECTION 11 TABLE 11.29 Equati
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11.88 SECTION 11 TABLE 11.29 Equati
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11.90 SECTION 11 The more stable th
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11.92 SECTION 11 11.6.6.2.5 Buffer
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11.94 SECTION 11 TABLE 11.30 Standa
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TABLE 11.32 Properties and Applicat
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11.98 SECTION 11 TABLE 11.36 Maskin
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11.100 SECTION 11 TABLE 11.37 Anion
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11.102 SECTION 11 TABLE 11.39 Amino
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11.104 SECTION 11 TABLE 11.44 Facto
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11.106 SECTION 11 11.7 LABORATORY S
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11.108 SECTION 11 TABLE 11.48 Stand
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11.110 SECTION 11 Alizarin yellow G
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11.112 SECTION 11 Bromchlorophenol
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11.114 SECTION 11 p-Ethoxychrysoidi
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11.116 SECTION 11 Mercurous nitrate
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11.118 SECTION 11 Potassium carbona
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11.120 SECTION 11 until the ammoniu
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11.122 SECTION 11 TABLE 11.49 TLV C
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11.130 SECTION 11 TABLE 11.50 Chemi
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11.138 SECTION 11 of water which is
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TABLE 11.55 Thermoelectric Values i
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TABLE 11.56 Type B Thermocouples: P
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TABLE 11.58 Type J Thermocouples: I
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TABLE 11.60 Type N Thermocouples: N
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TABLE 11.62 Type S Thermocouples: P
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11.150 SECTION 11 11.11 CORRECTION
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Index Terms Links 2 Acid-base indic
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Index Terms Links 4 Alkynes, nomenc
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Index Terms Links 6 Aurintricarboxy
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Index Terms Links 8 Boron-11 chemic
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Index Terms Links 10 Cellulose acet
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Index Terms Links 12 Collective ino
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Index Terms Links 14 Degree Fahrenh
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Index Terms Links 16 Electrical res
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Index Terms Links 18 Equivalent wei
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Index Terms Links 20 Fluorocarbon p
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Index Terms Links 22 Halogenated hy
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Index Terms Links 24 Impact strengt
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Index Terms Links 26 Kα 1 lines, m
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Index Terms Links 28 Melmine phenol
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Index Terms Links 30 Neon-neon bond
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Index Terms Links 32 One-tailed tes
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Index Terms Links 34 Physical chemi
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Index Terms Links 36 Polyolefin the
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Index Terms Links 38 Pyridine: bina
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Index Terms Links 40 Rho values: fo
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Index Terms Links 42 Single-bond ra
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Index Terms Links 44 Stereoisomers
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Index Terms Links 46 Tension, aqueo
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Index Terms Links 48 Triethylenetet
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Index Terms Links 50 Water (Cont.)
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