Cycloaddition reactivities analyzed by energy decomposition analyses and the frontier molecular orbital model

A Sengupta, B Li, D Svatunek, F Liu… - Accounts of Chemical …, 2022 - ACS Publications
Conspectus This Account describes our quest to understand and predict organic reactivity, a
principal goal of physical and theoretical organic chemistry. The focus is on the development …

Mechanisms and substituent effects of metal-free bioorthogonal reactions

T Deb, J Tu, RM Franzini - Chemical reviews, 2021 - ACS Publications
Reactions that occur under physiological conditions find diverse uses in the chemical and
biological sciences. However, the limitations that biological systems place on chemical …

A simple method of identifying π orbitals for non-planar systems and a protocol of studying π electronic structure

T Lu, Q Chen - Theoretical Chemistry Accounts, 2020 - Springer
The characteristic of π electrons has a crucial role in determining various properties of
chemical systems, such as reactivity, aromaticity and spectroscopy. There are a large …

Unraveling tetrazine-triggered bioorthogonal elimination enables chemical tools for ultrafast release and universal cleavage

JCT Carlson, H Mikula… - Journal of the American …, 2018 - ACS Publications
Recent developments in bond cleavage reactions have expanded the scope of
bioorthogonal chemistry beyond click ligation and enabled new strategies for probe …

Bioorthogonal cycloadditions: computational analysis with the distortion/interaction model and predictions of reactivities

F Liu, Y Liang, KN Houk - Accounts of chemical research, 2017 - ACS Publications
Conspectus Bioorthogonal chemistry has had a major impact on the study of biological
processes in vivo. Biomolecules of interest can be tracked by using probes and reporters …

Optimized tetrazine derivatives for rapid bioorthogonal decaging in living cells

X Fan, Y Ge, F Lin, Y Yang, G Zhang… - Angewandte …, 2016 - Wiley Online Library
The inverse‐electron‐demand Diels–Alder (iDA) reaction has recently been repurposed as
a bioorthogonal decaging reaction by accelerating the elimination process after an initial …

Quantum Tunneling Instability in Pericyclic Reactions

A Frenklach, H Amlani, S Kozuch - Journal of the American …, 2024 - ACS Publications
Several cycloreversion reactions of the retro-Diels–Alder type were computationally
assessed to understand their quantum tunneling (QT) reactivity. N2, CO, and other leaving …

Computational Studies of Reactions of 1, 2, 4, 5-Tetrazines with Enamines in MeOH and HFIP

P Ma, D Svatunek, Z Zhu, DL Boger… - Journal of the …, 2024 - ACS Publications
The reaction between 1, 2, 4, 5-tetrazines and alkenes in polar solvents proceeds through a
Diels–Alder cycloaddition along the C–C axis (C3/C6 cycloaddition) of the tetrazine …

Regioselective pyridine to benzene edit inspired by water-displacement

BR Boswell, Z Zhao, RL Gonciarz… - Journal of the American …, 2024 - ACS Publications
Late-stage derivatization of drug-like functional groups can accelerate drug discovery efforts
by swiftly exchanging hydrogen-bond donors with acceptors, or by modulating key …

Solid-state pathway control via reaction-directing heteroatoms: ordered pyridazine nanothreads through selective cycloaddition

SG Dunning, L Zhu, B Chen, S Chariton… - Journal of the …, 2022 - ACS Publications
Nanothreads are one-dimensional nanomaterials composed of a primarily sp3 hydrocarbon
backbone, typically formed through the compression of small molecules to high pressures …