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Computational Approaches for the Prediction of pKa Values book cover

1st Edition

Computational Approaches for the Prediction of pKa Values

By George C. Shields, Paul G. Seybold Copyright 2014
175 Pages 25 B/W Illustrations
by CRC Press

175 Pages 25 B/W Illustrations
by CRC Press

175 Pages
by CRC Press
Also available as eBook on:
The pK a of a compound describes its acidity or basicity and, therefore, is one of its most important properties. Its value determines what form of the compound—positive ion, negative ion, or neutral species—will be present under different circumstances. This is crucial to the action and detection of the compound as a drug, pollutant, or other active chemical agent. In many cases it is desirable... Read more

Introduction

Absolute pKa Calculations
Thermodynamic Cycles
Gas Phase Gibbs Free Energy Calculations
Solvation Gibbs Free Energy Calculations
Pitfalls and Lessons from the Literature
Concluding Remarks on Absolute pKa Calculations

Relative pKa Calculations

Quantitative Structure-Acidity Relationships (QSARs)
Basic Principles of the QSAR approach
Hammett and Taft Constants
The Search for Useful Quantum Chemical Descriptors
Alternative Approaches
Commercial and Free Programs

Oxyacids and Related Compounds
Alcohols, Phenols, and Carboxylic Acids
Phosphonic Acids
Hydroxamic Acids and Oximes
Silanols
Thiols

Nitrogen Acids
Aliphatic Amines
Anilines
Azoles and Some Other Heterocyclics
Amino Acids
Pyridines and Related Heterocyclics
Purines and Pyrimidines

Additional Types of Acids
Carbon Acids
Inorganic Acids
Polyprotic Acids
Superacids
Excited State Acids

Acids in Non-aqueous Solvents
Deuterium Oxide
Dimethyl Sulfoxide
Acetonitrile
Tetrahydrofuran
1,2-Dichloroethane
Other Solvents and Commentary

Additional Factors Influencing Acidity and Basicity
Thermodynamics
Temperature Effects on Acidity
Steric Effects and Hydrogen Bonding
Isotope Effects

Conclusions

Biography

George Shields, Ph.D., is currently a professor of chemistry and dean of the College of Arts and Sciences at Bucknell University. His research uses computational chemistry to investigate atmospheric and biological chemistry.

Paul Seybold, Ph.D., has been has been a faculty member and department chair (1999–2004) in the Department of Chemistry at Wright State University in Ohio and a visiting scholar and visiting professor at a number of universities in the United States and Europe. His research interests center on chemical and biochemical applications of quantum chemistry, molecular structure-activity relationships, luminescence spectroscopy, and cellular automata models of complex systems.

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