Spectroscopic, XRD, Hirshfeld surface and density functional theory (DFT) studies of the non-covalent interactions in 2-hydroxy-3-iodo-5-nitroacetophenone

2-hydroxy-5-nitroacetophenone ( 1 ) reacted with N-iodosuccinimide in acetic acid at room temperature to afford 2-hydroxy-3-iodo-5-nitroacetophenone ( 2 ). Structural elucidation was carried out using a combination of spectroscopic and single crystal X-ray diffraction (XRD) techniques complemented with DFT method. The hydroxyl proton resonates significantly downfield at delta H = 13.80 ppm due to participation in intramolecular hydrogen bonding, which resulted in a not easy to discern low intensity infrared band located in the region of the nu(CH) vibrations 280 0-30 0 0 cm -1. XRD analysis confirmed the presence of a chair-like six-membered hydrogen bonded pseudo aromatic ring involving O -H ... = C interaction. Prediction model (Hirshfeld surface and 2D fingerprint model) was performed to understand the intermolecular interactions responsible for the molecular packing in the crystal of 2 . (c) 2022 Elsevier B.V. All rights reserved.

Automated summary

The structure of 2-hydroxy-3-iodo-5-nitroacetophenone was elucidated using spectroscopic and X-ray diffraction techniques, revealing the presence of intramolecular hydrogen bonding and interaction with the O atom, forming a chair-like six-membered hydrogen bonded pseudo aromatic ring.