Themed collection Computational Organic Chemistry

18 items
Editorial

Introduction to Computational Organic Chemistry

Jonathan Goodman, Jolene Reid and Judy Wu introduce the Organic & Biomolecular Chemistry themed collection on Computational Organic Chemistry.

Graphical abstract: Introduction to Computational Organic Chemistry
From the themed collection: Computational Organic Chemistry
Open Access Communication

On the mechanism of carboxylate elimination from carbohydrate monoester-derived radicals

Computational analysis of the HAT-induced expulsion of carboxylic acids from monoacylated pyranosides implicates concerted elimination through a hydrogen-bonded transition state.

Graphical abstract: On the mechanism of carboxylate elimination from carbohydrate monoester-derived radicals
From the themed collection: Computational Organic Chemistry
Open Access Paper

Computational methods for investigating organic radical species

Computational analysis of organic radical species presents significant challenges. This study compares the efficacy of various DFT and wavefunction methods in predicting radical stabilisation energies, bond dissociation energies, and redox potentials.

Graphical abstract: Computational methods for investigating organic radical species
From the themed collection: Computational Organic Chemistry
Paper

Intermolecular hydrogen bonding behavior of amino acid radical cations

DFT calculations revealed the structural and energetic impact of oxidation on major intermolecular hydrogen-bonding modes of amino acids.

Graphical abstract: Intermolecular hydrogen bonding behavior of amino acid radical cations
From the themed collection: Computational Organic Chemistry
Paper

Exploring the mechanism of the reductive amination of acetophenones via the Borch approach: the role of the acid catalyst

In the reductive amination process, the acid catalyst plays a crucial role not only in the elimination of water but also in the nucleophilic step, particularly when electron-donating groups are installed at the para-position of the acetophenone.

Graphical abstract: Exploring the mechanism of the reductive amination of acetophenones via the Borch approach: the role of the acid catalyst
From the themed collection: Computational Organic Chemistry
Paper

Binding of the plant-derived toxin simplexin to bovine protein kinase C: insights from molecular dynamics

Pimelea poisoning of Australian cattle is attributed to the natural toxin simplexin binding to bovine PKC. Molecular dynamics simulations reveal simplexin's high affinity for PKC, and identify SAR for future molecular interventions against poisoning.

Graphical abstract: Binding of the plant-derived toxin simplexin to bovine protein kinase C: insights from molecular dynamics
From the themed collection: Computational Organic Chemistry
Paper

Molecular dynamics and NMR reveal the coexistence of H-bond-assisted and through-space JFH coupling in fluorinated amino alcohols

The JFH coupling constants in fluorinated amino alcohols were investigated through experimental and theoretical approaches.

Graphical abstract: Molecular dynamics and NMR reveal the coexistence of H-bond-assisted and through-space JFH coupling in fluorinated amino alcohols
From the themed collection: Computational Organic Chemistry
Paper

Tetraquinolines; four linked quinoline units or porphyrinoids

3D current density distribution in TEQ2+ suggests a transformation from antiaromaticity to aromaticity.

Graphical abstract: Tetraquinolines; four linked quinoline units or porphyrinoids
From the themed collection: Computational Organic Chemistry
Paper

A theoretical study on radical scavenging activity of phenolic derivatives naturally found within Alternaria alternata extract

The antioxidant mechanisms and properties of four dibenzopyrone phenolic compounds from Alternaria alternata are studied using DFT, molecular docking, and dynamics studies.

Graphical abstract: A theoretical study on radical scavenging activity of phenolic derivatives naturally found within Alternaria alternata extract
From the themed collection: Computational Organic Chemistry
Open Access Paper

Dehydration of alcohols catalyzed by copper(II) sulfate: type II dyotropic reactions and stepwise mechanisms

Dehydration of alcohols by CuSO4 can take place via (asynchronous) concerted or stepwise mechanisms. DFT calculations show the effect of the substitution pattern of the starting alcohol on the actual mechanism.

Graphical abstract: Dehydration of alcohols catalyzed by copper(ii) sulfate: type II dyotropic reactions and stepwise mechanisms
From the themed collection: Computational Organic Chemistry
Paper

Theoretical insights into the enantiodivergence induced by chiral phosphoric acid catalysis with a Lewis acid for the synthesis of N–N axially chiral atropisomers

A detailed theoretical mechanistic investigation on the enantiodivergence of chiral phosphoric acid-catalyzed Paal–Knorr reactions with/without a Lewis acid for the synthesis of N–N axially chiral atropisomers is described.

Graphical abstract: Theoretical insights into the enantiodivergence induced by chiral phosphoric acid catalysis with a Lewis acid for the synthesis of N–N axially chiral atropisomers
From the themed collection: Computational Organic Chemistry
Paper

Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects

DFT calculations show that the tautomeric equilibria of 2- and 4-pyridones are controlled by different effects and can be modulated by substituents and medium polarity. A more polar medium favours the more polar lactam form.

Graphical abstract: Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects
From the themed collection: Computational Organic Chemistry
Paper

Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing an endocyclic heteroatom

We report the synthesis of heterobiarylcyclooctynes bearing an endocyclic heteroatom, oxa-azabenzobenzocyclooctynes (O-ABCs).

Graphical abstract: Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing an endocyclic heteroatom
From the themed collection: Computational Organic Chemistry
Paper

Exploring α-electron-deficiency-induced [1,2]-fluorine migration

The α-electron-deficiency-induced [1,2]-fluorine migration reaction follows a concerted mechanism with a tight-ion-pair transition state. When coupled with other reaction units, mechanistic variants are asynchronously concerted.

Graphical abstract: Exploring α-electron-deficiency-induced [1,2]-fluorine migration
From the themed collection: Computational Organic Chemistry
Open Access Paper

Strengthened cooperativity of DNA-based cyclic hydrogen-bonded rosettes by subtle functionalization

Cooperative effects cause extra stabilization of hydrogen-bonded supramolecular systems.

Graphical abstract: Strengthened cooperativity of DNA-based cyclic hydrogen-bonded rosettes by subtle functionalization
From the themed collection: Computational Organic Chemistry
Open Access Paper

Understanding the reactivity and selectivity of Diels–Alder reactions involving furans

The origins of the reactivity and endo/exo selectivity of the Diels–Alder cycloaddition reactions involving furan and substituted furans as dienes have been computationally explored.

Graphical abstract: Understanding the reactivity and selectivity of Diels–Alder reactions involving furans
From the themed collection: Computational Organic Chemistry
Paper

Effects of phosphine ligands in nickel-catalyzed decarbonylation reactions of lactone

It is the electronic effect of the phosphine ligands that plays a dominant role in the Ni-catalyzed decarbonylation reactions.

Graphical abstract: Effects of phosphine ligands in nickel-catalyzed decarbonylation reactions of lactone
From the themed collection: Computational Organic Chemistry
Paper

Design rules for optimization of photophysical and kinetic properties of azoarene photoswitches

The E-isomer λmax and Z-isomer t1/2 have been simultaneously optimized for a set of 26 hemi-azothiophenes. We found that by incorporating cross-conjugated thiophenes and additional π-conjugation, these two properties can be leveraged.

Graphical abstract: Design rules for optimization of photophysical and kinetic properties of azoarene photoswitches
From the themed collection: Computational Organic Chemistry
18 items

About this collection

This themed issue guest edited by Professor Jonathan Goodman (University of Cambridge), Professor Jolene Reid (University of British Columbia) and Professor Judy Wu (University of Houston), aims to highlight some of the excellent research currently happening in the field of computational organic chemistry, providing explanations, predictions and insights for the reactivity, structure, functions, and properties of organic systems.

New articles will be added to the collection upon publication. Please return to this page frequently to see the collection grow.

Spotlight

Advertisements