LANGE'S HANDBOOK OF CHEMISTRY

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ORGANIC COMPOUNDS 1.29 to 9N(O)9; theprefix ONN- specifies that the first of these two groups is attached directly to 9N(O)9. When only one parent compound is cited in the name, the prefixed ONN- and NNOspecify that the group carrying the primed and unprimed substituents is connected, respectively, to the 9N(O)9 group. Theprefix NON- signifies that the position of the oxygen atom is unknown; the azoxy group is then written as 9N 2O9. For example, 2,2,4-Trichloro-NNO-azoxybenzene 1.1.3.11 Boron Compounds. Molecular hydrides of boron are called boranes. They are named by using a multiplying affix to designate the number of boron atoms and adding an Arabic numeral within parentheses as a suffix to denote the number of hydrogen atoms present. Examples are pentaborane(9) for B 5H 9 and pentaborane(11) for B 5H 11. Organic ring systems are named by replacement nomenclature. Three- to ten-membered monocyclic ring systems containing uncharged boron atoms may be named by the specialist nomenclature for heterocyclic systems. Organic derivatives are named as outlined for substitutive nomenclature. The complexity of boron nomenclature precludes additional details; the text by Rigaudy and Klesney should beconsulted. 1.1.3.12 Carboxylic Acids. Carboxylic acids may be named in several ways. First, 9COOH groups replacing CH 39 at the end of the main chain of an acyclic hydrocarbon are denoted by adding -oic acid to thenameof thehydrocarbon. Second, when the9COOH group is theprincipal group, thesuffix -carboxylic acid can beadded to thenameof theparent chain whosenameand chain numbering does not include thecarbon atom of the9COOH group. The former nomenclature is preferred unless use of the ending -carboxylic acid leads to citation of a larger number of carboxyl groups as suffix. Third, carboxyl groups are designated by the prefix carboxy- when attached to a group named as a substituent or when another group is present that has higher priority for citation as principal group. In all cases, the principal chain should be linked to as many carboxyl groups as possible even though it might not be the longest chain present. Examples are CH CH CH CH CH CH COOH (1) Heptanoic acid 3 2 2 2 2 2 (2) 1-Hexanecarboxylic acid C H COOH (2) Cyclohexanecarboxylic acid 6 11 (3) 2-(Carboxymethyl)-1,4-hexanedicarboxylic acid Removal of the OH from the 9COOH group to form theacyl radical results in changing the ending -oic acid to -oyl or the ending -carboxylic acid to -carbonyl. Thus the radical CH 3CH 2CH 2CH 2CO9 is named either pentanoyl or butanecarbonyl. When the hydroxyl has not been removed from all carboxyl groups present in an acid, the remaining carboxyl groups are denoted by the prefix carboxy-. For example, HOOCCH 2CH 2CH 2CH 2CH 2CO9 is named 6-carboxyhexanoyl.
1.30 SECTION 1 TABLE 1.11 Names of Some Carboxylic Acids Systematic name Trivial name Systematic name Trivial name Methanoic Formic trans-Methylbutenedioic Mesaconic* Ethanoic Acetic Propanoic Propionic 1,2,2-Trimethyl-1,3-cyclopen- Camphoric Butanoic Butyric tanedicarboxylic acid 2-Methylpropanoic Isobutyric* Pentanoic Valeric Benzenecarboxylic Benzoic 3-Methylbutanoic Isovaleric* 1,2-Benzenedicarboxylic Phthalic 2,2-Dimethylpropanoic Pivalic* 1,3-Benzenedicarboxylic Isophthalic Hexanoic (Caproic) 1,4-Benzenedicarboxylic Terephthalic Heptanoic (Enanthic) Naphthalenecarboxylic Naphthoic Octanoic (Caprylic) Methylbenzenecarboxylic Toluic Decanoic (Capric) 2-Phenylpropanoic Hydratropic Dodecanoic Lauric* 2-Phenylpropenoic Atropic Tetradecanoic Myristic* trans-3-Phenylpropenoic Cinnamic Hexadecanoic Palmitic* Furancarboxylic Furoic Octadecanoic Stearic* Thiophenecarboxylic Thenoic 3-Pyridinecarboxylic Nicotinic Ethanedioic Oxalic 4-Pyridinecarboxylic Isonicotinic Propanedioic Malonic Butanedioic Succinic Hydroxyethanoic Glycolic Pentanedioic Glutaric 2-Hydroxypropanoic Lactic Hexanedioic Adipic 2,3-Dihydroxypropanoic Glyceric Heptanedioic Pimelic* Hydroxypropanedioic Tartronic Octanedioic Suberic* Hydroxybutanedioic Malic Nonanedioic Azelaic* 2,3-Dihydroxybutanedioic Tartaric Decanedioic Sebacic* 3-Hydroxy-2-phenylpropanoic Tropic Propenoic Acrylic 2-Hydroxy-2,2-diphenyl- Benzilic Propynoic Propiolic ethanoic 2-Methylpropenoic Methacrylic 2-Hydroxybenzoic Salicylic trans-2-Butenoic Crotonic Methoxybenzoic Anisic cis-2-Butenoic Isocrotonic 4-Hydroxy-3-methoxybenzoic Vanillic cis-9-Octadecenoic Oleic trans-9-Octadecenoic Elaidic 3,4-Dimethoxybenzoic Veratric cis-Butenedioic Maleic 3,4-Methylenedioxybenzoic Piperonylic trans-Butenedioic Fumaric 3,4-Dihydroxybenzoic Protocatechuic cis-Methylbutenedioic Citraconic* 3,4,5-Trihydroxybenzoic Gallic * Systematic names should be used in derivatives formed by substitution on a carbon atom. Note: The names in parentheses are abandoned but are listed for reference to older literature. Many trivial names exist for acids; these are listed in Table 1.11. Generally, radicals are formed by replacing -ic acid by -oyl.* When a trivial name is given to an acyclic monoacid or diacid, the numeral 1 is always given as locant to the carbon atom of a carboxyl group in the acid or to the carbon atom with a free valence in the radical RCO9. * Exceptions: formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, oxalyl, malonyl, succinyl, glutaryl, furoyl, and thenoyl.
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 27 and 28: 1.14 SECTION 1 TABLE 1.5 Trivial Na
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Page 37 and 38: 1.24 SECTION 1 heterocyclic structu
Page 39 and 40: 1.26 SECTION 1 Bivalent radicals of
Page 41: 1.28 SECTION 1 Complex linear polya
Page 45 and 46: 1.32 SECTION 1 hydroxyamino- to the
Page 47 and 48: 1.34 SECTION 1 may be named (1) by
Page 49 and 50: 1.36 SECTION 1 Examples are methyl
Page 51 and 52: 1.38 SECTION 1 tuted acid, respecti
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Page 57 and 58: 1.44 SECTION 1 FIGURE 1.11 Two isom
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
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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. 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
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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
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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
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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:
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Index Terms Links Specific gravity:
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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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