Computational Organic Chemistry (eBook)

STEVEN M. BACHRACH is the Dr. D. R. Semmes Distinguished Professor of Chemistry at Trinity University. Dr. Bachrach has published some 125 articles. With the support of the National Science Foundation and the Welch Foundation, he researches computational approaches to build our understanding of nucleophilic substitution reactions and the role of solvents.

Acknowledgements

Preface

Preface to the First Edition

1. Quantum Mechanics for Organic Chemistry

1.1 Approximations to the Schrödinger Equation - the Hartree Fock Method

1.2 Electron Correlation - Post-Hartree-Fock Methods

1.3 Density Functional Theory (DFT)

1.4 Computational Approaches to Solvation

1.5 Hybrid QM/MM methods

1.6 Potential Energy Surfaces

1.7 Population Analysis

1.8. Interview: Stefan Grimme

1.9 References

2. Computed Spectral Properties and Structure Identification

2.1 Computed Bond Lengths and Angles

2.2 IR spectroscopy

2.3 Nuclear Magnetic Resonance

2.4 Optical Rotation, Optical Rotatory Dispersion, Electronic Circular Dichroism and Vibrational Circular Dichroism

2.5 Interview: Jonathan Goodman

2.6 References

3. Fundamentals of Organic Chemistry

3.1 Bond Dissociation Enthalpy

3.2 Acidity

3.3 Isomerism and Problems with DFT

3.4 Ring Strain Energy

3.5 Aromaticity

3.6 Interview: Professor Paul von Ragué Schleyer

3.7 References

4. Pericyclic Reactions

4.1 The Diels-Alder Reaction

4.2 The Cope Rearrangement

4.3 The Bergman Cyclization

4.4 Bispericyclic Reactions

4.5 Pseudopericyclic Reactions

4.6 Torquoselectivity

4.7 Interview: Professor Weston Thatcher Borden

4.8 References

5. Diradicals and Carbenes

5.1 Methylene

5.2 Phenylnitrene and Phenylcarbene

5.3 Tetramethyleneethane

5.4 Oxyallyl diradical

5.5 Benzynes

5.6 Tunneling of Carbenes

5.7 Interview: Professor Henry "Fritz" Schaefer

5.8 Interview: Professor Peter R. Schreiner

5.9 References

6. Organic Reactions of Anions

6.1 Substitution Reactions

6.2 Asymmetric Induction via 1,2-Addition to Carbonyl Compounds

6.3 Asymmetric Organocatalysis of Aldol Reactions

6.4 Interview - Professor Kendall N. Houk

6.5 References

7. Solution-Phase Organic Chemistry

7.2 Glucose

7.3 Nucleic Acids

7.4 Amino Acids

7.5 Interview: Professor Christopher J. Cramer

7.6 References

8. Organic Reaction Dynamics

8.1 A Brief Introduction to Molecular Dynamics Trajectory Computations

8.2 Statistical Kinetic Theories

8.3 Examples of Organic Reactions with Non-statistical Dynamics

8.4 Conclusions

8.5 Interview: Professor Daniel Singleton

8.6 References

9. Computational Approaches to Understanding Enzymes

9.1 Models for enzymatic activity

9.2 Strategy for computational enzymology

9.3 De Novo Design of Enzymes

9.4 References

"Valuable for anyone wishing to learn how to carry out quantum chemistry computations. . .Highly recommended. Upper-division undergraduates and above." (Choice, 1 June 2015)

"The Second Edition of author Steven Bachrach's highly acclaimed Computational Organic Chemistry reflects the tremendous advances in computational methods since the publication of the First Edition, explaining how these advances have shaped our current understanding of organic chemistry." (Chemistry Views, 23 October 2014)