Introduction | p. iii |
Water Solubility and Chemical Bonding | p. 1 |
Van der Waals Attraction (Forces) | p. 1 |
Dipole-Dipole Bonding (Hydrogen Bond) | p. 2 |
Ionic Attraction | p. 3 |
Ion-Dipole Bonding | p. 4 |
Alkanes (C[subscript n]H[subscript 2n+2]) | p. 6 |
Alkenes (C[subscript n]H[subscript 2 n]) | p. 11 |
Cycloalkanes: Alkene Isomers | p. 14 |
Aromatic Hydrocarbons | p. 16 |
Halogenated Hydrocarbons | p. 19 |
Alcohols | p. 21 |
Phenols | p. 25 |
Ethers | p. 30 |
Aldehydes and Ketones | p. 33 |
Amines | p. 38 |
Quaternary Ammonium Salts | p. 46 |
Carboxylic Acids | p. 48 |
Functional Derivatives of Carboxylic Acids | p. 56 |
Esters | p. 56 |
Amides | p. 59 |
Carbonates, Carbamates, and Ureas | p. 62 |
Amidines and Guanidines | p. 64 |
Sulfonic Acids and Sulfonamides | p. 66 |
Sulfonic Acids | p. 66 |
Sulfonamides | p. 66 |
Thioethers and Nitro Groups | p. 69 |
Thioethers | p. 69 |
Nitro Groups | p. 70 |
Heterocycles | p. 71 |
Three-Membered Ring Heterocycles | p. 71 |
Four-Membered Ring Heterocycles | p. 74 |
Five-Membered Ring Heterocycles | p. 75 |
Five-Membered Ring Heterocycles With Two or More Heteroatoms | p. 80 |
Six-Membered Ring Heterocycles | p. 87 |
Six-Membered Ring Heterocycles With Two Heteroatoms | p. 88 |
Saturated Six-Membered Heterocycles | p. 94 |
Seven- And Eight-Membered Ring Heterocycles | p. 94 |
Bicyclic Heterocycles: Five-Membered Ring Plus Six-Membered Ring | p. 95 |
Bicyclic Heterocycles: Six-Membered Ring Plus Six-Membered Ring | p. 100 |
Bicyclic Heterocycles: Six-Membered Ring Plus Seven-Membered Ring | p. 103 |
Tricyclic Heterocycles | p. 104 |
Oligonucleotides and Nucleic Acids | p. 106 |
Proteins | p. 112 |
Predicting Water Solubility | p. 122 |
Empiric Method | p. 122 |
Analytic Method | p. 126 |
Stereoisomerism--Asymmetric Molecules | p. 129 |
Acidity and Basicity | p. 132 |
Definitions of Acids and Bases | p. 132 |
Relative Strengths of Acids and Bases | p. 134 |
Reaction of an Acid With a Base in Water | p. 136 |
Acidic and Basic Organic Function Groups | p. 138 |
Drug Metabolism | p. 141 |
Oxygenase Enzymes | p. 141 |
Hydrolase Enzymes | p. 145 |
Conjugation Reactions | p. 145 |
Index | p. 149 |
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