![]() Let’s see how this applies to a simple acid-base reaction between hydrochloric acid and fluoride ion: Recall that the driving force for a reaction is usually based on two factors: relative charge stability, and relative total bond energy. The pK a of the thiol group on the cysteine side chain, for example, is approximately 8.3, while the pKa for the alcohol group on the serine side chain is on the order of 17. More importantly to the study of biological organic chemistry, this trend tells us that thiols are more acidic than alcohols. HI, with a pKa of about -9, is almost as strong as sulfuric acid. ![]() Because fluoride is the least stable (most basic) of the halide conjugate bases, HF is the least acidic of the haloacids, only slightly stronger than a carboxylic acid. For now, we are applying the concept only to the influence of atomic radius on base strength. We will see this idea expressed again and again throughout our study of organic reactivity, in many different contexts. Chapter 2: Electronic Structure and Periodic Properties of ElementsĢ.4 Electronic Structure of Atoms (Electron Configurations)Ģ.5 Periodic Variations in Element PropertiesĬhapter 3: Chemical Bonding and Molecular GeometryĬhapter 4: Advanced Theories of Covalent BondingĬhapter 6: Introduction to Organic Structure and Bondingħ.4 Structural Effects on Acidity and Basicityħ.6 Acid-Base Properties of Nitrogen-Containing Functional Groupsħ.9 Effects of Enzyme Microenvironment on Acidity and BasicityĬhapter 8: Conformation and StereochemistryĨ.3 Stereochemistry of Organic Compounds and PharmaceuticalsĮlectrostatic charges, whether positive or negative, are more st able when they are “spread out” over a larger area.
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