The Library
Mapping of N−C bond formation from a series of crystalline peri‐substituted naphthalenes by charge density and solid‐state NMR methodologies
Tools
Tools
Tools
Rees, Gregory J., Pitak, Mateusz B., Lari, Alberth, Day, Stephen Paul, Yates, Jonathan R., Gierth, Peter, Barnsley, Kristian E., Smith, Mark E., Coles, Simon J., Hanna, John V. and Wallis, John D. (2021) Mapping of N−C bond formation from a series of crystalline peri‐substituted naphthalenes by charge density and solid‐state NMR methodologies. Angewandte Chemie International Edition, 60 (44). pp. 23878-23884. doi:10.1002/anie.202111100 ISSN 1433-7851.
|
PDF
WRAP-Mapping-N-CBond-series-crystalline-peri-substituted-naphthalenes-density-solid-state-2021.pdf - Published Version - Requires a PDF viewer. Available under License Creative Commons Attribution 4.0. Download (2259Kb) | Preview |
Official URL: https://doi.org/10.1002/anie.202111100
Abstract
A combination of charge density studies and solid state nuclear magnetic resonance (NMR) 1JNC coupling measurements supported by periodic density functional theory (DFT) calculations is used to characterise the transition from an n–π* interaction to bond formation between a nucleophilic nitrogen atom and an electrophilic sp2 carbon atom in a series of crystalline peri‐substituted naphthalenes. As the N⋅⋅⋅C distance reduces there is a sharp decrease in the Laplacian derived from increasing charge density between the two groups at ca. N⋅⋅⋅C = 1.8 Å, with the periodic DFT calculations predicting, and heteronuclear spin‐echo NMR measurements confirming, the 1JNC couplings of ≈3–6 Hz for long C−N bonds (1.60–1.65 Å), and 1JNC couplings of <1 Hz for N⋅⋅⋅C >2.1 Å.
| Item Type: | Journal Article | |||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Subjects: | Q Science > QD Chemistry | |||||||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Physics | |||||||||
| SWORD Depositor: | Library Publications Router | |||||||||
| Library of Congress Subject Headings (LCSH): | Chemistry, Inorganic, Chemical bonds, Nuclear magnetic resonance spectroscopy -- Methodology | |||||||||
| Journal or Publication Title: | Angewandte Chemie International Edition | |||||||||
| Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA | |||||||||
| ISSN: | 1433-7851 | |||||||||
| Official Date: | 25 October 2021 | |||||||||
| Dates: |
|
|||||||||
| Volume: | 60 | |||||||||
| Number: | 44 | |||||||||
| Page Range: | pp. 23878-23884 | |||||||||
| DOI: | 10.1002/anie.202111100 | |||||||||
| Status: | Peer Reviewed | |||||||||
| Publication Status: | Published | |||||||||
| Access rights to Published version: | Open Access (Creative Commons) | |||||||||
| Date of first compliant deposit: | 29 October 2021 | |||||||||
| Date of first compliant Open Access: | 2 November 2021 | |||||||||
| RIOXX Funder/Project Grant: |
|
|||||||||
| Related URLs: |
Request changes or add full text files to a record
Repository staff actions (login required)
 |
View Item |
Downloads
Downloads per month over past year
