Issue 36, 2019

Intramolecular π–hole interactions with nitro aromatics

Abstract

A thorough evaluation of the CSD and DFT computations were conducted to assess if intramolecular π–hole interactions can stabilize a conformer of nitro aromatics. It was found that this can only be the case when the nitro N-atom and an interacting electron-rich atom are separated by at least four bonds. Data from the solid state correspond well to the gas phase calculations and stabilizing energies were estimated to be as large as about 2–3 kcal mol−1, which is in the order of weak hydrogen bonding interactions.

Graphical abstract: Intramolecular π–hole interactions with nitro aromatics

Supplementary files

Article information

Article type
Paper
Submitted
29 Jun 2019
Accepted
07 Aug 2019
First published
07 Aug 2019
This article is Open Access
Creative Commons BY-NC license

CrystEngComm, 2019,21, 5410-5417

Intramolecular π–hole interactions with nitro aromatics

A. Franconetti, A. Frontera and T. J. Mooibroek, CrystEngComm, 2019, 21, 5410 DOI: 10.1039/C9CE01015G

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