Tools
Tools
Wallis, J.D. 
ORCID: 0000-0001-7259-8783, Addicoat, M. ORCID: 0000-0002-5406-7927 and Bristow, J.,
2019.
O(-)---C interactions and bond formation in 1-naphtholate anions with peri-located electrophilic carbon centres.
CrystEngComm.
ISSN 1466-8033
|
Text
13065_Wallis.pdf - Post-print Download (818kB) | Preview |
Abstract
The first peri interactions between naphtholate oxyanions and electrophilic double bonds are described. Tetramethylguanidine forms crystalline salts with 8-acetyl- and 8-benzoyl-naphthol which show O---C distances for the anions in the range 2.558-2.618 Å and small increases in carbonyl pyramidalities over the corresponding naphthols, whereas DMAP forms only hydrogen bonded complexes. Replacement of the acyl group with an alkene leads to intramolecular O-C bond formation for just the most electron deficient alkenes, with long peri O-C bonds (1.508 and 1.521 Å) observed in one case. However, both cyclised and uncyclised examples can be deprotonated to give cyclic structures according to NMR, and DFT calculations suggest very long peri- O-C bond lengths of 1.540 and 1.622 Å for two of these anions.
| Item Type: | Journal article | ||||
|---|---|---|---|---|---|
| Publication Title: | CrystEngComm | ||||
| Creators: | Wallis, J.D., Addicoat, M. and Bristow, J. | ||||
| Publisher: | Royal Society of Chemistry | ||||
| Date: | 9 January 2019 | ||||
| ISSN: | 1466-8033 | ||||
| Identifiers: |
|
||||
| Divisions: | Schools > School of Science and Technology | ||||
| Record created by: | Linda Sullivan | ||||
| Date Added: | 11 Jan 2019 15:24 | ||||
| Last Modified: | 11 Jan 2019 15:24 | ||||
| URI: | https://irep.ntu.ac.uk/id/eprint/35530 |
Actions (login required)
 |
Edit View |
Views
Views per month over past year
Downloads
Downloads per month over past year
