Farrell, David, Kingston, Samuel, Tungulin, Dmitri, Nuzzo, Stefano, Twamley, Brendan, Platts, James A. ![]() |
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Abstract
A series of 10-[(4-halo-2,6-diisopropylphenyl)imino]phenanthren-9-ones and derivatives of the phenanthrene-9,10-dione ligand have been synthesised and structurally characterised to explore two types of noncovalent interactions, namely the influence of the steric bulk upon the resulting C–H···π and π-stacking interactions and halogen bonding. Selected noncovalent interactions have additionally been analysed by DFT and AIM techniques. No halogen bonding has been observed in these systems, but X lone pair···π, C–H···O=C and C–H···π interactions are the prevalent ones in the halogenated systems. Removal of the steric bulk in N-(2,4,6-trimethylphenyl)-9,10-iminophenanthrenequinone affords different noncovalent interactions, but the C–H···O=C hydrogen bonds are observed. Surprisingly, in N-(2,6-dimethylphenyl)-9,10-iminophenanthrenequinone and N-(phenyl)-9,10-iminophenanthrenequinone these C–H···O=C hydrogen bonds are not observed. However, they are observed in the related 2,6-di-tert-butylphenanthrene-9,10-dione. The π-interactions in dimers extracted from the crystal structures have been analysed by DFT and AIM. Spectroscopic investigations are also presented and these show only small perturbations to the O=C–C=N fragment.
Item Type: | Article |
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Date Type: | Publication |
Status: | Published |
Schools: | Chemistry |
Publisher: | Wiley |
ISSN: | 1434-193X |
Date of First Compliant Deposit: | 31 August 2017 |
Date of Acceptance: | 15 August 2017 |
Last Modified: | 04 Dec 2024 05:45 |
URI: | https://orca.cardiff.ac.uk/id/eprint/104178 |
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