Intramolecular π-hole interactions with nitro aromatics

Antonio Franconetti; Antonio Frontera; Tiddo J. Mooibroek

doi:10.1039/c9ce01015g

Intramolecular π-hole interactions with nitro aromatics

Antonio Franconetti, Antonio Frontera, Tiddo J. Mooibroek^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Research › peer-review

20 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5410-5417
Number of pages	8
Journal	CrystEngComm
Volume	21
Issue number	36
DOIs	https://doi.org/10.1039/c9ce01015g
Publication status	Published - 2019
Externally published	Yes

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title = "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.",

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AU - Frontera, Antonio

AU - Mooibroek, Tiddo J.

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AB - 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.

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DO - 10.1039/c9ce01015g

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Intramolecular π-hole interactions with nitro aromatics

Abstract

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