Probing Halogen-π versus CH-π Interactions in Molecular Balance

Jie Jian; Jordi Poater; Paul B. White; Christine J. Mckenzie; F. Matthias Bickelhaupt; Jasmin Mecinović

doi:10.1021/acs.orglett.0c02773

Probing Halogen-π versus CH-π Interactions in Molecular Balance

Jie Jian, Jordi Poater, Paul B. White, Christine J. Mckenzie, F. Matthias Bickelhaupt, Jasmin Mecinović

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Abstract

Molecular balances based on the dibenzobicyclo[3.2.2]nonane template enable probing of the competition between halogen-π and CH-π interactions. Structural, NMR spectroscopic, and computational analyses revealed that the π system can favorably interact both with C-X or C-H functionalities, depending on the size of the functional group.

Original language	English
Pages (from-to)	7870-7873
Number of pages	4
Journal	Organic letters
Volume	22
Issue number	20
Early online date	29 Sept 2020
DOIs	https://doi.org/10.1021/acs.orglett.0c02773
Publication status	Published - 16 Oct 2020

Funding

We thank The Netherlands Organization for Scientific Research (NWO) for financial support. J.J. thanks the China Scholarship Council (CSC201808440511), and J.P. thanks the Spanish MINECO (PID2019-106830GB-I00 and MDM-2017-0767) and the Generalitat de Catalunya (2017SGR348). The Carlsberg Foundation is acknowledged for funding of the X-ray diffractometer (CF15-0675).

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/acs.orglett.0c02773

Probing Halogen−π versus CH−π Interactions in Molecular BalanceFinal published version, 1.13 MBLicence: Article 25fa Dutch Copyright Act

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AU - Bickelhaupt, F. Matthias

AU - Mecinović, Jasmin

PY - 2020/10/16

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N2 - Molecular balances based on the dibenzobicyclo[3.2.2]nonane template enable probing of the competition between halogen-π and CH-π interactions. Structural, NMR spectroscopic, and computational analyses revealed that the π system can favorably interact both with C-X or C-H functionalities, depending on the size of the functional group.

AB - Molecular balances based on the dibenzobicyclo[3.2.2]nonane template enable probing of the competition between halogen-π and CH-π interactions. Structural, NMR spectroscopic, and computational analyses revealed that the π system can favorably interact both with C-X or C-H functionalities, depending on the size of the functional group.

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Probing Halogen-π versus CH-π Interactions in Molecular Balance

Abstract

Funding

UN SDGs

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CCDC 2004049: Experimental Crystal Structure Determination

CCDC 2004050: Experimental Crystal Structure Determination

CCDC 2004051: Experimental Crystal Structure Determination

Cite this

Probing Halogen-π versus CH-π Interactions in Molecular Balance

Abstract

Funding

UN SDGs

Access to Document

Persistent URL (handle)

Other files and links

Fingerprint

Datasets

CCDC 2004049: Experimental Crystal Structure Determination

CCDC 2004050: Experimental Crystal Structure Determination

CCDC 2004051: Experimental Crystal Structure Determination

Cite this