4.6 Article

Universal Trends between Acid Dissociation Constants in Protic and Aprotic Solvents

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Multidisciplinary

How to Predict the pKa of Any Compound in Any Solvent

Michael Busch et al.

Summary: The acid-base properties of molecules in nonaqueous solvents are crucial in various fields of chemistry, but our knowledge on the pK(a) values is limited. This paper presents a computational method to predict pK(a) values in any solvent, using only experimental pK(a) of a reference compound in water and quantum-chemical calculations. The method is tested and validated by computing proton solvation energy in different solvents and comparing the pK(a) values of simple compounds. The results show that the method is robust and efficient.

ACS OMEGA (2022)

Review Chemistry, Physical

Determination of the absolute solvation free energy and enthalpy of the proton in solutions

Alhadji Malloum et al.

Summary: This article discusses the importance of absolute solvation energies of solutes in solution and methods for evaluating these energies. The study shows that these absolute solvation energies are crucial for determining the acids proton dissociation constant of organic compounds, as well as for the development of continuum solvation models and force fields. While the absolute solvation energies of solutes cannot be determined experimentally, they can be assessed through various methods.

JOURNAL OF MOLECULAR LIQUIDS (2021)

Article Chemistry, Physical

Solvation free energy of the proton in acetonitrile

Alhadji Malloum et al.

Summary: In this study, the solvation free energy of the proton in acetonitrile was calculated using the cluster continuum solvation model, with an estimated value of -1022.0 kJmol(-1) at the MP2/CBS level of theory. The results showed excellent agreement with the experimental estimate based on the tetraphenylarsonium-tetraphenylborate (TATB) approach.

JOURNAL OF MOLECULAR LIQUIDS (2021)

Article Chemistry, Physical

From absolute potentials to a generalized computational standard hydrogen electrode for aqueous and non-aqueous solvents

Michael Busch et al.

Summary: This study presents a new method for calculating the conversion factor of the absolute potential of the standard hydrogen electrode in various solvents, unaffected by experimental shortcomings. By combining the absolute potential in water with the conversion factor, the potential in other solvents can be accurately predicted. Experimental validation in 36 solvents shows that the relative absolute potentials vary with solvent polarity and hydrogen bonding ability.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2021)

Review Chemistry, Organic

On the Basicity of Organic Bases in Different Media

Sofja Tshepelevitsh et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Rapid and Accurate Prediction of pKa Values of C-H Acids Using Graph Convolutional Neural Networks

Rafal Roszak et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Physical

Rigorous pK(a) Estimation of Amine Species Using Density-Functional Tight-Binding-Based Metadynamics Simulations

Aditya Wibawa Sakti et al.

JOURNAL OF CHEMICAL THEORY AND COMPUTATION (2018)

Article Chemistry, Physical

A Systematic Theoretical Study on the Acidities for Cations of Ionic Liquids in Dimethyl Sulfoxide

Zhen Wang et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2018)

Article Chemistry, Organic

pKa values in organic chemistry - Making maximum use of the available data

Agnes Kutt et al.

TETRAHEDRON LETTERS (2018)

Article Chemistry, Physical

Solvation energies of the proton in methanol revisited and temperature effects

Alhadji Malloum et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2018)

Article Chemistry, Physical

Prediction of pKa Values for Druglike Molecules Using Semiempirical Quantum Chemical Methods

Jan H. Jensen et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2017)

Article Chemistry, Physical

Computing pKa Values in Different Solvents by Electrostatic Transformation

Emanuele Rossini et al.

JOURNAL OF CHEMICAL THEORY AND COMPUTATION (2016)

Correction Chemistry, Multidisciplinary

Proton solvation in protic and aprotic solvents (vol 37, pg 1082, 2015)

Emanuele Rossini et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Proton solvation in protic and aprotic solvents

Emanuele Rossini et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2016)

Article Chemistry, Physical

Acid-base equilibrium dynamics in methanol and dimethyl sulfoxide probed by two-dimensional infrared spectroscopy

Chiho Lee et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2015)

Review Chemistry, Multidisciplinary

Redox Potentials and Acidity Constants from Density Functional Theory Based Molecular Dynamics

Jun Cheng et al.

ACCOUNTS OF CHEMICAL RESEARCH (2014)

Article Chemistry, Multidisciplinary

Predicting pKa in Implicit Solvents: Current Status and Future Directions

Junming Ho

AUSTRALIAN JOURNAL OF CHEMISTRY (2014)

Article Chemistry, Analytical

Cathodic Stripping Determination of Water in Organic Solvents

Changlong Xiao et al.

ELECTROANALYSIS (2014)

Review Chemistry, Physical

Theoretical pKa Calculations With Continuum Model Solvents, Alternative Protocols to Thermodynamic Cycles

Rodrigo Casasnovas et al.

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY (2014)

Article Biochemistry & Molecular Biology

Toward the accurate calculation of pKa values in water and acetonitrile

James T. Muckerman et al.

BIOCHIMICA ET BIOPHYSICA ACTA-BIOENERGETICS (2013)

Article Chemistry, Organic

Acidities of strong neutral Bronsted acids in different media

Elin Raamat et al.

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY (2013)

Review Chemistry, Multidisciplinary

Solvatochromic parameters for solvents of interest in green chemistry

Philip G. Jessop et al.

GREEN CHEMISTRY (2012)

Article Chemistry, Organic

Scales of Oxidation Potentials, pKa, and BDE of Various Hydroquinones and Catechols in DMSO

Xiao-Qing Zhu et al.

JOURNAL OF ORGANIC CHEMISTRY (2010)

Review Chemistry, Physical

A universal approach for continuum solvent pK(a) calculations: are we there yet?

Junming Ho et al.

THEORETICAL CHEMISTRY ACCOUNTS (2010)

Article Chemistry, Multidisciplinary

The ionic work function and its role in estimating absolute electrode potentials

W. Ronald Fawcett

LANGMUIR (2008)

Review Chemistry, Multidisciplinary

First-principle predictions of absolute pKa's of organic acids in dimethyl sulfoxide solution

Y Fu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

Article Chemistry, Multidisciplinary

Basicity of nucleophilic carbenes in aqueous and nonaqueous solvents-theoretical predictions

AM Magill et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

Article Chemistry, Physical

Origin of the overpotential for oxygen reduction at a fuel-cell cathode

JK Norskov et al.

JOURNAL OF PHYSICAL CHEMISTRY B (2004)

Review Chemistry, Multidisciplinary

Gibbs energies of transfer of cations from water to mixed aqueous organic solvents

C Kalidas et al.

CHEMICAL REVIEWS (2000)