Reaction Heats and Bond Strengths

Based on a Series of Lectures Given to Postgraduate Students at the University of Keele, 1960

1st Edition - January 1, 1962
Author: C. T. Mortimer
Language: English
eBook ISBN:
9 7 8 - 1 - 4 8 3 1 - 8 6 5 0 - 4

Reaction Heats and Bond Strengths presents the variations in the heats of particular types of reaction. This book covers a variety of topics, including the hydrogenation and… Read more

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Reaction Heats and Bond Strengths presents the variations in the heats of particular types of reaction. This book covers a variety of topics, including the hydrogenation and polymerization of olefinic compounds, the dissociation of organic and organo-metallic compounds, and the molecular-addition compounds. Organized into 10 chapters, this book begins with an overview of the concept of bond energy that can be very useful where a comparison is being made between two dissimilar molecules. This text then examines the strain in cyclopropane and cyclobutane, which is largely a result of angular strain due to compression of the tetrahedral angle in the carbon–carbon bonding. Other chapters consider the experimental thermochemical data for some conjugated molecules. This book discusses as well the significance of representing a molecule, which originated from the concept of resonance. The final chapter deals with bond strength in phosphorus, silicon, and sulfur compounds. This book is a valuable resource for postgraduate students.

1. The Thermochemical Approach

Introduction

Energy changes in Heats of Reaction

Definitions of Bond Strength

1. Bond Energies

2. Bond Dissociation Energies

Heats of Reaction

Experimental Methods

2. Strain Energies in Saturated and Unsaturated Organic Compounds

Saturated Cyclic Compounds

1. Cyclo-alkanes

2. Heterocyclic Compounds

3. Decalins

4. Perhydroanthracenes

5. Dimethylcyclohexanes

6. Dimethylcyclopentanes

7. Hydrindanes

Unsaturated Compounds

1. Cyclic Olefins

2. Cyclic or^o-Substituted Benzene Derivatives

3. Acyclic Olefins

Polycyclo-alkanes and Alkenes

Exo-Endo Isomerism in Olefins

Conclusion

3. Stabilization Energiesm in Non-Aromatic Compounds

Introduction

Conjugation and Hyper conjugation

1. Olefins

2. Acetylenes

Polar Effects

Hybridization

Conclusion

4. Strain and Resonance Energies in Aromatic Compounds

Introduction

Experimental Determination of Resonance Energies

1. Bond Compressional Energy

2. Hybridization Changes

3. Charge Separation

4. Steric Effects

Five- and Seven-membered Ring Systems

Four- and Eight-membered Ring Systems

Cat a-Condensed Hydrocarbons

Polycyclic Hydrocarbons

1. Stabilization Energies

2. Strain Energies

Hetero-aromatics

Conclusion

5. Polymerization Energies

Heats of Self-Polymerization Reactions

Free Energies and Entropies

Co-polymerization

Polymerization of Cyclic Compounds

1. Cyclo-alkanes

2. Heterocyclic Compounds

6. Molecular Addition Compounds

Introduction

Steric and Inductive Effects

Acceptor Molecules: n-Bonding

Donor Molecules: Donor Strength and Reorganization Energy

Addition compounds: ^-Bonding

1. Acceptor Atoms with Available d-Orbitals

2. Acceptor Atoms with pseudo pπ-Orbitals

Conclusion

7. Bond Dissociation Energies and Heats of Formation of Free Radicals

Introduction

Heats of Formation of Free Radicals

1. Alkyl Radicals

2. Vinyl Radical

3. Benzyl Radical

4. Phenyl Radical

5. Cyanide Radical

6. Halogen-substituted Alkyl Radicals

7. Alkoxy Radicals

8. Thioalkoxy Radicals

9. Alkyl Amino Radicals

10. Radicals RCOO

Stepwise Dissociation Energies

8. Metal-Carbon and Metal-Halogen Bonds

Introduction

Mean Bond Dissociation Energies

1. Representative and 6-Group Elements

2. Transition Metals, Carbonyls

3. Cyclopentadienyl and Benzene Compounds

Stepwise Dissociation Energies

1. b-Group Metal Alkyls

2. Transition Metal Halides

Summary

9. Ionization Energies in Aqueous Solution

Introduction

Heats of Neutralization of Strong Acids and Strong Bases

Aliphatic Acids

Methyl-substituted Compounds

1. Picolines

2. Cresols

3. Chlorophenols

4. Nitrophenols

5. Toluidines

6. Methyl-Benzoic Acids

7. Lutidines and Xylenols

8. Summary of Data for Methyl-substituted Compounds

Halogen Substituted Acetic Acids

Dibasic Organic Acids

Conclusion

10. Bond Strengths in Silicon, Phosphorus and Sulfur Compounds

Introduction

dπ-pπ-Bonding in Simple Molecules

1. Silicon

2. Phosphorus

3. Sulfur

dπ-pπ-Bonding in Cyclic Systems

1. Cyclic Phosphazenes

2. Sulphanuric and Thiazyl Compounds

References

Author Index

Subject Index