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^*

^*Corresponding author for this work

Department of Physics, Chemistry and Pharmacy

Research output: Contribution to journal › Journal article › Research › peer-review

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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
Journal	Organic Letters
Volume	22
Issue number	20
Pages (from-to)	7870-7873
ISSN	1523-7060
DOIs	https://doi.org/10.1021/acs.orglett.0c02773
Publication status	Published - 2020

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10.1021/acs.orglett.0c02773

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@article{445280b522b54c26b274372e28c25c2d,

title = "Probing Halogen−π versus CH−π Interactions in Molecular Balance",

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.",

author = "Jie Jian and Jordi Poater and White, {Paul B.} and McKenzie, {Christine J.} and Bickelhaupt, {F. Matthias} and Jasmin Mecinovi{\'c}",

year = "2020",

doi = "10.1021/acs.orglett.0c02773",

language = "English",

volume = "22",

pages = "7870--7873",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "20",

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TY - JOUR

T1 - Probing Halogen−π versus CH−π Interactions in Molecular Balance

AU - Jian, Jie

AU - Poater, Jordi

AU - White, Paul B.

AU - McKenzie, Christine J.

AU - Bickelhaupt, F. Matthias

AU - Mecinović, Jasmin

PY - 2020

Y1 - 2020

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.

U2 - 10.1021/acs.orglett.0c02773

DO - 10.1021/acs.orglett.0c02773

M3 - Journal article

C2 - 32991183

VL - 22

SP - 7870

EP - 7873

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 20

ER -

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

Abstract

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