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N-Aryl-9,10-phenanthreneimines as scaffolds for exploring non-covalent interactions: a structural and computational study

Farrell, David, Kingston, Samuel, Tungulin, Dmitri, Nuzzo, Stefano, Twamley, Brendan, Platts, James A. and Baker, Robert J. 2017. N-Aryl-9,10-phenanthreneimines as scaffolds for exploring non-covalent interactions: a structural and computational study. European Journal of Organic Chemistry 2017 (37) , pp. 5597-5609. 10.1002/ejoc.201700884

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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
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: 10 Oct 2018 22:42
URI: http://orca.cf.ac.uk/id/eprint/104178

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