LANGE'S HANDBOOK OF CHEMISTRY

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ORGANIC COMPOUNDS 1.35 remain when each bridge is replaced by two hydrogen atoms. The locant for 9CO9 is cited before that for the ester oxygen atom. An additional carbon atom is incorporated into this structure as compared to the -olide. These trivial names are permitted: -butyrolactone, -valerolactone, and -valerolactone. Names based on heterocycles may be used for all lactones. Thus, -butyrolactoneis also tetrahydro-2furanoneor dihydro-2(3H)-furanone. Lactides, intermolecular cyclic esters, are named as heterocycles. Lactams and lactims, containing a 9CO9NH9 and 9C(OH)"N9 group, respectively, are named as heterocycles, but they may also be named with -lactam or -lactim in place of -olide. For example, (1) 2-Pyrrolidinone (2) 4-Butanelactam 1.1.3.20 Nitriles and Related Compounds. For acids whose systematic names end in -carboxylic acid, nitriles arenamed by adding thesuffix -carbonitrilewhen the9CN group replaces the 9COOH group. Thecarbon atom of the9CN group is excluded from the numbering of a chain to which it is attached. However, when the triple-bonded nitrogen atom is considered to replace three hydrogen atoms at the end of the main chain of an acyclic hydrocarbon, the suffix -nitrile is added to the name of the hydrocarbon. Numbering begins with the carbon attached to the nitrogen. For example, CH 3CH 2CH 2CH 2CH 2CN is named (1) pentanecarbonitrile or (2) hexanenitrile. Trivial acid names are formed by changing the endings -oic acid or -ic acid to -onitrile. For example, CH 3CN is acetonitrile. When the 9CN group is not thehighest priority group, the9CN group is denoted by the prefix cyano-. In order of decreasing priority for citation of a functional class name, and the prefix for substitutive nomenclature, are the following related compounds: Functional group Prefix Radicofunctional ending 9NC Isocyano- Isocyanide 9OCN Cyanato- Cyanate 9NCO Isocyanato- Isocyanate 9ONC — Fulminate 9SCN Thiocyanato- Thiocyanate 9NCS Isothiocyanato- Isothiocyanate 9SeCN Selenocyanato- Selenocyanate 9NCSe Isoselenocyanato- Isoselenocyanate 1.1.3.21 Peroxides. Compounds of thetypeR9O9OH arenamed (1) by placing thenameof theradical R beforetheword hydroperoxide or (2) by use of the prefix hydroperoxy- when another parent name has higher priority. For example, C 2H 5OOH is ethyl hydroperoxide. Compounds of thetypeR 1 O9OR 2 arenamed (1) by placing thenames of theradicals in alphabetical order before the word peroxide when the group 9O9O9 links two chains, two rings, or a ring and a chain, (2) by useof theaffix dioxy to denotethebivalent group 9O9O9 for naming assemblies of identical units or to form part of a prefix, or (3) by use of the prefix epidioxywhen the peroxide group forms a bridge between two carbon atoms, a ring, or a ring system.
1.36 SECTION 1 Examples are methyl propyl peroxide for CH 39O9O9C 3H 7 and 2,2-dioxydiacetic acid for HOOC9CH 29O9O9CH 29COOH. 1.1.3.22 Phosphorus Compounds. Acyclic phosphorus compounds containing only onephosphorus atom, as well as compounds in which only a single phosphorus atom is in each of several functional groups, are named as derivatives of the parent structures listed in Table 1.12. Often these TABLE 1.12 Parent Structures of Phosphorus-Containing Compounds Formula Parent name Substitutive prefix Radicofunctional ending H3P PhosphineH2P9 Phosphino- Phosphide H5P PhosphoraneH4P9 Phosphoranyl- H3P Phosphoroanediyl- H2P Phosphoranetriyl- H3PO Phosphineoxide H3PS Phosphinesulfide H3PNH Phosphineimide P(OH) 3 Phosphorous acid Phosphite HP(OH) 2 Phosphonous acid Phosphonite H2POH Phosphinous acid Phosphinite P(O)(OH) 3 Phosphoric acid P(O) Phosphoryl- Phosphate(V) HP(O)(OH) 2 Phosphonic acid HP(O) Phosphonoyl- Phosphonate H 2P(O)OH Phosphinic acid 9P(O)OH 2 H2P(O)9 P(O)OH Phosphono- Phosphinoyl- Phosphinoco- Phosphinato- Phosphinate are purely hypothetical parent structures. When hydrogen attached to phosphorus is replaced by a hydrocarbon group, the derivative is named by substitution nomenclature. When hydrogen of an 9OH group is replaced, the derivative is named by radicofunctional nomenclature. For example, C 2H 5PH 2 is ethylphosphine; (C 2H 5) 2PH, diethylphosphine; CH 3P(OH) 2, dihydroxy-methyl-phosphineor methylphosphonous acid; C 2H 59PO(Cl)(OH), ethylchlorophosphonic acid or ethylphosphonochloridic acid or hydrogen chlorodioxoethylphosphate(V); CH 3CH(PH 2)COOH, 2-phosphinopropionic acid; HP(CH 2COOH) 2, phosphinediyldiacetic acid; (CH 3)HP(O)OH, methylphosphinic acid or hydrogen hydridomethyldioxophosphate(V); (CH 3O) 3PO, trimethyl phosphate; and (CH 3O) 3P, trimethyl phosphite. 1.1.3.23 Salts and Esters of Acids. Neutral salts of acids are named by citing the cation(s) and then the anion, whose ending is changed from -oic to -oate or from -ic to -ate. When different acidic residues are present in one structure, prefixes are formed by changing the anion ending -ate to -atoor -ide to -ido-. The prefix carboxylato- denotes the ionic group 9COO . Thephrase(metal) salt of (the acid) is permissible when the carboxyl groups are not all named as affixes. Acid salts includetheword hydrogen (with affixes, if appropriate) inserted between the name of thecation and thenameof theanion (or word salt). Esters arenamed similarly, with thenameof thealkyl or aryl radical replacing thenameof the
Page 1 and 2: LANGE'S HANDBOOK OF CHEMISTRY John
Page 3 and 4: Grateful acknowledgment is hereby m
Page 5 and 6: PREFACE TO FIFTEENTH EDITION This n
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Page 9 and 10: xii PREFACE TO FOURTEENTH EDITION l
Page 11 and 12: PREFACE TO FIRST EDITION This book
Page 13 and 14: For the detailed contents of any se
Page 15 and 16: 1.2 SECTION 1 is derived from the G
Page 17 and 18: 1.4 SECTION 1 rather than methylide
Page 19 and 20: 1.6 SECTION 1 Styrene Toluene Xylen
Page 21 and 22: 1.8 SECTION 1 TABLE 1.2 Fused Polyc
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Page 37 and 38: 1.24 SECTION 1 heterocyclic structu
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Page 41 and 42: 1.28 SECTION 1 Complex linear polya
Page 43 and 44: 1.30 SECTION 1 TABLE 1.11 Names of
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Page 51 and 52: 1.38 SECTION 1 tuted acid, respecti
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Page 59 and 60: 1.46 SECTION 1 Chiral Center. The c
Page 61 and 62: 1.48 SECTION 1 FIGURE 1.15 Isomers
Page 63 and 64: 1.50 SECTION 1 entries to bring tog
Page 65 and 66: 1.52 SECTION 1 TABLE 1.13 Names and
Page 73 and 74: 1.60 SECTION 1 TABLE 1.14 Empirical
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Page 91 and 92: 2.4 SECTION 2 TABLE 2.1 Fundamental
Page 93 and 94: 2.6 SECTION 2 TABLE 2.1 Fundamental
Page 95 and 96: 2.8 SECTION 2 TABLE 2.2 Physical an
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2.12 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. To find t
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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 Molar Equ
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2.92 SECTION 2 TABLE 2.19 Factors f
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2.94 SECTION 2 TABLE 2.19 Factors f
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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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3.16 TABLE 3.2 Physical Constants o
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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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4.5 Silver (argentum) Ag 47 [Kr] 4d
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PROPERTIES OF ATOMS,RADICALS,AND BO
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PROPERTIES OF ATOMS, RADICALS, AND
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TABLE 4.5 Electronegativities of th
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TABLE 4.11 Bond Dissociation Energi
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TABLE 4.16 Table of Nuclides (Conti
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SECTION 5 PHYSICAL PROPERTIES 5.1 S
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5.1 SOLUBILITIES PHYSICAL PROPERTIE
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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(CHO2) 2 26.2 28.0 29.9 31
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(III) sulfateCe2(SO4) 3 ·9H2O 21.4
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iodidePbI2 0.044 0.056 0.069 0.090
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Nickel sulfateNiSO4 ·6H2O (pale bl
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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 98 107
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TABLE 5.3 Vapor Pressure of Mercury
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TABLE 5.4 Vapor Pressure of Ice in
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TABLE 5.6 Vapor Pressure of Water (
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TABLE 5.8 Vapor Pressures of Variou
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PHYSICAL PROPERTIES 5.33 TABLE 5.8
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5.3 BOILING POINTS TABLE 5.10 Boili
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TABLE 5.11 Binary Azeotropic (Const
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TABLE 5.12 Ternary Azeotropic Mixtu
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5.4 FREEZING MIXTURES TABLE 5.13 Co
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TABLE 5.13 Compositions of Aqueous
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5.5 DENSITY AND SPECIFIC GRAVITY TA
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PHYSICAL PROPERTIES 5.89 d D t t
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5.6.1 Refractive Index PHYSICAL PRO
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PHYSICAL PROPERTIES 5.137 where the
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5.7 COMBUSTIBLE MIXTURES TABLE 5.23
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TABLE 5.23 Properties of Combustibl
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Deuterium 1150 1222 1297 1372 1448
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TABLE 5.25 Liquid Thermal Conductiv
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TABLE 5.26 Thermal Conductivity of
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TABLE 5.29 Van der Waals’ Constan
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TABLE 5.30 Triple Points of Various
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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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PClF 3 THERMODYNAMIC PROPERTIES 6.1
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THERMODYNAMIC PROPERTIES 6.143 The
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TABLE 6.5 Critical Properties (Cont
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SECTION 7 SPECTROSCOPY 7.1 X-RAY ME
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TABLE 7.1 Wavelengths of X-Ray Emis
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SPECTROSCOPY 7.5 TABLE 7.1 Waveleng
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TABLE 7.2 Wavelengths of Absorption
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TABLE 7.3 Critical X-Ray Absorption
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TABLE 7.4 X-Ray Emission Energies i
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SPECTROSCOPY 7.13 Emission line K 1
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TABLE 7.7 Analyzing Crystals for X-
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SPECTROSCOPY 7.17 TABLE 7.8 Mass Ab
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TABLE 7.9 Electronic Absorption Ban
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TABLE 7.11 Absorption Wavelength of
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SPECTROSCOPY 7.23 TABLE 7.13 Solven
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7.3 FLUORESCENCE TABLE 7.16 Fluores
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SPECTROSCOPY 7.27 TABLE 7.16 Fluore
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TABLE 7.18 Detection Limits in ng/m
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TABLE 7.19 Sensitive Lines of the E
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TABLE 7.19 Sensitive Lines of the E
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In terms of m, the wavenumber of m
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The ionization constant can be calc
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SPECTROSCOPY 7.43 TABLE 7.20 Absorp
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TABLE 7.22 Absorption Frequencies o
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TABLE 7.27 Absorption Frequencies i
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TABLE 7.28 Infrared Transmitting Ma
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7.69
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7.6 RAMAN SPECTROSCOPY SPECTROSCOPY
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SPECTROSCOPY 7.73 TABLE 7.30 Raman
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SPECTROSCOPY 7.75 TABLE 7.30 Raman
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TABLE 7.32 Raman Frequencies of Cum
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TABLE 7.33 Raman Frequencies of Car
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TABLE 7.34 Raman Frequencies of Oth
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TABLE 7.35 Raman Frequencies of Aro
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TABLE 7.36 Raman Frequencies of Sul
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TABLE 7.39 Raman Frequencies of Mis
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7.7 NUCLEAR MAGNETIC RESONANCE TABL
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TABLE 7.41 Nuclear Properties of th
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TABLE 7.42 Proton Chemical Shifts (
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SPECTROSCOPY 7.95 TABLE 7.44 Estima
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TABLE 7.46 Proton Spin Coupling Con
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SPECTROSCOPY 7.99 TABLE 7.48 Solven
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TABLE 7.49 Carbon-13 Chemical Shift
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SPECTROSCOPY 7.103 TABLE 7.51 Effec
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TABLE 7.54 Carbon-13 Chemical Shift
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TABLE 7.56 One-Bond Carbon-Hydrogen
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TABLE 7.58 Carbon-Carbon Spin Coupl
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7 Li CH3Li 15 SPECTROSCOPY 7.111 TA
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TABLE 7.63 Nitrogen-15 (or Nitrogen
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TABLE 7.64 Nitrogen-15 Chemical Shi
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TABLE 7.69 Fluorine-19 Chemical Shi
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TABLE 7.72 Silicon-29 Chemical Shif
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TABLE 7.73 Phosphorus-31 Chemical S
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TABLE 7.74 Phosphorus-31 Spin Coupl
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when z 3 and y 1. The empirical f
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Masses 19 and 31 Alcohol Mass 66
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TABLE 7.76 Condensed Table of Mass
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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 8.25 Fluorescent Indicators (
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3,3-Dimethoxybenzidine dihydrochlor
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8.7 CONDUCTANCE ELECTROLYTES, EMF,
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TABLE 8.35 Equivalent Conductivitie
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KCl 127.3 124.4 122.4 115.8 112.0 1
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NaIO 3 75.2 72.6 70.9 64.4 60.5 1
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Conductance of an Electrolyte Solut
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9.2 SECTION 9 9.1 LINEAR FREE ENERG
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9.4 SECTION 9 TABLE 9.1 Hammett and
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9.6 SECTION 9 TABLE 9.1 Hammett and
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9.8 SECTION 9 TABLE 9.3 pKa and Rho
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10.2 SECTION 10 10.4.6 Polyacrylate
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10.4 SECTION 10 10.2 ADDITIVES TO P
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10.6 SECTION 10 injection molding.
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10.8 SECTION 10 10.3 FORMULAS AND K
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10.10 SECTION 10 Key properties of
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10.12 SECTION 10 10.3.8 Fluorocarbo
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10.14 SECTION 10 10.3.11 Phenolics
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10.16 SECTION 10 The resin has the
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10.18 SECTION 10 10.3.19 Polyuretha
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10.20 SECTION 10 10.3.22 Sulfones B
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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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11.1 COOLING TABLE 11.1 Cooling Mix
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11.2 DRYING AND HUMIDIFICATION TABL
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PRACTICAL LABORATORY INFORMATION 11
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TABLE 11.7 Relative Humidity from D
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3-Methyl-1-butanol 132.0 Cyclohexyl
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TABLE 11.9 Molecular Elevation of t
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TABLE 11.11 Solvents of Chromatogra
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TABLE 11.13 McReynolds’ Constants
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FIGURE 11.1 Profile of a solute ban
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TABLE 11.16 Guide to Ion-Exchange R
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TABLE 11.16 Guide to Ion-Exchange R
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11.5 GRAVIMETRIC ANALYSIS TABLE 11.
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TABLE 11.19 Gravimetric Factors (Co
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Sodium tetraphenylborate, NaB(C 6H
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TABLE 11.24 Porosities of Fritted G
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TABLE 11.26 HeatingTemperatures, Co
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TABLE 11.28 Titrimetric (Volumetric
Page 1169 and 1170:
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HN 3 PRACTICAL LABORATORY INFORMATI
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11.6.5 Precipitation Titrations PRA
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TABLE 11.31 Indicators for Precipit
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TABLE 11.33 Variation of 4 with pH
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TABLE 11.38 Common Demasking Agents
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TABLE 11.41 Pipet Capacity Toleranc
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TABLE 11.45 Cubical Coefficients of
Page 1197 and 1198:
TABLE 11.48 Standard Stock Solution
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TABLE 11.48 Standard Stock Solution
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11.8 SIEVES AND SCREENS TABLE 11.53
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TABLE 11.55 Thermoelectric Values i
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TABLE 11.57 Type E Thermocouples: N
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TABLE 11.59 Type K Thermocouples: N
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TABLE 11.61 Type R Thermocouples: P
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TABLE 11.63 Type T Thermocouples: C
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Index Terms Links Abbreviations: of
Page 1243 and 1244:
Index Terms Links Aggregation, stat
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Index Terms Links Anions, inorganic
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Index Terms Links Benzoylacetone, f
Page 1249 and 1250:
Index Terms Links Carbon-carbon: bo
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Index Terms Links Chemical shifts:
Page 1253 and 1254:
Index Terms Links Correction for so
Page 1255 and 1256:
Index Terms Links Dielectric streng
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Index Terms Links Emergent stem cor
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Index Terms Links Excitation wavele
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Index Terms Links Gases: equations
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Index Terms Links Hydrogen: binary
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Index Terms Links Iodine: bond diss
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Index Terms Links Lithium: bond dis
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Index Terms Links Mode for set of n
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Index Terms Links Nitrogen-oxygen d
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Index Terms Links Peak asymmetry fa
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Index Terms Links Polybutylene poly
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Index Terms Links Precipitates, hea
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Index Terms Links Rankine scale, co
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Index Terms Links Selection rules:
Page 1283 and 1284:
Index Terms Links Specific gravity:
Page 1285 and 1286:
Index Terms Links Sulfuric acid sol
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Index Terms Links Thiosulfate: form
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Index Terms Links Vaporization: ent
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Index Terms Links Zincon, formation
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LANGE'S HANDBOOK OF CHEMISTRY

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