Blueprints for the Geometric Control of N-Heterocyclic Carbene–Carbodiimide Isomers
Name
ChemistryEurope - 2025 - Day - Blueprints for the Geometric Control of N‐Heterocyclic Carbene Carbodiimide Isomers (1).pdf
Description
Published version
Size
1.25 MB
Format
Adobe PDF
Checksum (MD5)
428ff7d589aa2689467bf4b05b69eaa5
Author(s)
Day, Craig S
Grabicki, Niklas
Chu, Daniel BK
Keys, Allison
Singhal, Avni
Vennelakanti, Vyshnavi
Kevlishvili, Ilia
Gómez‐Bombarelli, Rafael
Kulik, Heather J
Johnson, Jeremiah
Date Issued
May 20, 2025
Journal
ChemistryEurope
Publisher
Wiley
Citation
Day, Craig S, Grabicki, Niklas, Chu, Daniel BK, Keys, Allison, Singhal, Avni et al. 2025. "Blueprints for the Geometric Control of N-Heterocyclic Carbene–Carbodiimide Isomers." ChemistryEurope, 3 (4).
Version
Final published version
Abstract
Rational control of the 3D presentation of atoms—stereochemistry—lies at the heart of synthetic organic and materials chemistries. Here, researchers report detailed computational studies on conformational isomerism in N-heterocyclic carbene–carbodiimide (NHC–CDI) zwitterionic adducts. By varying the steric and electronic parameters of the NHC and CDI components, criteria for controlling isomerization thermodynamics and predicting energetically favorable conformations are identified. These criteria is validated experimentally using a novel synthetic approach to NHC–CDIs, which exploits the thermodynamic equilibrium between sterically unencumbered NHC dimers to access NHC–CDI adducts with low barriers to conformational isomerization, including the first example of an (E/E)-NHC–CDI.
MIT Department
Massachusetts Institute of Technology. Department of Chemical Engineering
Massachusetts Institute of Technology. Department of Chemistry
Massachusetts Institute of Technology. Computational and Systems Biology Program
Massachusetts Institute of Technology. Department of Materials Science and Engineering
Terms of Use
Creative Commons Attribution
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1002/ceur.202500023
