Themed collection Computational Organic Chemistry

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

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.

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

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.

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.

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

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

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

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.

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.

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.

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

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.

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

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.

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

The E-isomer λ^max and Z-isomer t_1/2 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.