Halogen Bonds between 2,2,6,6-Tetramethylpiperidine-N-oxyl Radical and CxHyFzI Species: DFT Calculations of Physicochemical Properties and Comparison with Hydrogen Bonded Adducts
- 1 August 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Physical Chemistry A
- Vol. 111 (34), 8482-8490
- https://doi.org/10.1021/jp073567b
Abstract
Structural, thermodynamic, and magnetic properties of adducts between the 2,2,6,6-tetramethylpiperidine-N-oxyl radical and representative hydrogen and halogen bond donors in solution have been investigated by an integrated computational tool including hybrid density functionals and discrete-continuum solvent models. From a quantitative point of view, the computed values show a fair agreement with experiment when environmental effects are taken into the proper account. From a more general point of view, our analysis points out a number of analogies, but also some difference, between hydrogen and halogen bond, which have been interpreted in terms of the various effects tuning thermodynamic and spectroscopic parameters.Keywords
This publication has 68 references indexed in Scilit:
- Halogen Bonding Based Recognition Processes: A World Parallel to Hydrogen BondingAccounts of Chemical Research, 2005
- Characterization of the Walker A Motif of MsbA Using Site-Directed Spin Labeling Electron Paramagnetic Resonance SpectroscopyBiochemistry, 2005
- Halogen bonds in biological moleculesProceedings of the National Academy of Sciences, 2004
- Halogen Bonding: A New Interaction for Liquid Crystal FormationJournal of the American Chemical Society, 2003
- Micellar aggregation of sulfonate surfactants studied by electron paramagnetic resonance of a cationic nitroxide: an experimental and computational approachPhysical Chemistry Chemical Physics, 2002
- The Persistent Radical Effect: A Principle for Selective Radical Reactions and Living Radical PolymerizationsChemical Reviews, 2001
- New Polymer Synthesis by Nitroxide Mediated Living Radical PolymerizationsChemical Reviews, 2001
- Fluorine-Containing Donor−Acceptor Complex: Infinite Chain Formed by Oxygen···Iodine InteractionJournal of the American Chemical Society, 2001
- Halogen Bonding: A Paradigm in Supramolecular ChemistryChemistry – A European Journal, 2001
- Halogen Bonding versus Hydrogen Bonding in Driving Self-Assembly ProcessesAngewandte Chemie-International Edition, 2000