An Assessment of Theoretical Protocols for Calculation of the pKa Values of the Prototype Imidazolium Cation-Reference-Cited by-同舟云学术

An Assessment of Theoretical Protocols for Calculation of the pKa Values of the Prototype Imidazolium Cation

Published:2004 Issue:12 Volume:57 Page:1205
ISSN:0004-9425
Container-title:Australian Journal of Chemistry
language:en
Short-container-title:Aust. J. Chem.

Author:

Magill Alison M.,Yates Brian F.

Abstract

The highly accurate complete basis set method CBS-QB3 has been used in conjunction with the conductor-like polarized continuum (CPCM) method to predict the aqueous pKa values for the three different hydrogen atoms in the imidazolium cation. Excellent agreement was obtained with the available experimental values. The pKa for the deprotonation of imidazole was also calculated and found to be quite different from the experimental estimate. The protocol for the pKa calculation was carefully analyzed and some recommendations made about the choice of levels of theory.

Publisher

CSIRO Publishing

Subject

General Chemistry

Link

http://www.publish.csiro.au/CH/pdf/CH04159

Reference66 articles.

1. pKa Values of Amines in Water from Quantum Mechanical Calculations Using a Polarized Dielectric Continuum Representation of the Solvent

2. Calculation of Absolute and Relative Acidities of Substituted Imidazoles in Aqueous Solvent

3. Short, Strong Hydrogen Bonds in the Gas Phase and in Solution: Theoretical Exploration of pKa Matching and Environmental Effects on the Strengths of Hydrogen Bonds and Their Potential Roles in Enzymatic Catalysis

4. Ab Initio Quantum Chemical Studies of the pKa's of Hydroxybenzoic Acids in Aqueous Solution with Special Reference to the Hydrophobicity of Hydroxybenzoates and Their Binding to Surfactants

5. Ab initio quantum mechanical calculations of p Kas of isolated molecules and molecules undergoing chemical reactions: p Ka of acetic acid during α-proton abstraction

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