Arene-Perfluoroarene Interactions in Solution
Publication type: Journal Article
Publication date: 2021-06-02
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
34077211
Organic Chemistry
Abstract
A systematic study of arene-perfluoroarene interactions in solution is presented. Using a combination of NMR titration experiments, X-ray crystallography, and computational analysis, we analyze the effects of fluorination, substituents, ring size, and solvation on the arene-perfluoroarene interaction. We find that fluorination, extension of the π systems, and enhancement of solvent polarity greatly stabilize the stacking energy up to 3 orders of magnitude (Ka = <1 to 6000 M-1), with the highest Ka achieved for the interaction of water-soluble variants of perfluoronaphthalene and anthracene in buffered D2O (pD = 12). Combining computational and experimental results, we conclude that this impressive binding energy is a result of enthalpically favorable electrostatic and dispersion interactions as well as the entropically driven hydrophobic effect. The enhanced understanding of arene-perfluoroarene interactions in aqueous solution sets the stage for the implementation of this abiotic intermolecular interaction in biology and medicine.
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Metrics
51
Total citations:
51
Citations from 2025:
14
(27.45%)
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GOST
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LEE G. et al. Arene-Perfluoroarene Interactions in Solution // Journal of Organic Chemistry. 2021. Vol. 86. No. 12. pp. 8425-8436.
GOST all authors (up to 50)
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LEE G., Hu E., Rheingold A. L., Houk K. N., Sletten E. M. Arene-Perfluoroarene Interactions in Solution // Journal of Organic Chemistry. 2021. Vol. 86. No. 12. pp. 8425-8436.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.1c00921
UR - https://doi.org/10.1021/acs.joc.1c00921
TI - Arene-Perfluoroarene Interactions in Solution
T2 - Journal of Organic Chemistry
AU - LEE, GA-YOUNG
AU - Hu, Elizabeth
AU - Rheingold, Arnold L.
AU - Houk, K. N.
AU - Sletten, Ellen M
PY - 2021
DA - 2021/06/02
PB - American Chemical Society (ACS)
SP - 8425-8436
IS - 12
VL - 86
PMID - 34077211
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2021_LEE,
author = {GA-YOUNG LEE and Elizabeth Hu and Arnold L. Rheingold and K. N. Houk and Ellen M Sletten},
title = {Arene-Perfluoroarene Interactions in Solution},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.joc.1c00921},
number = {12},
pages = {8425--8436},
doi = {10.1021/acs.joc.1c00921}
}
Cite this
MLA
Copy
LEE, GA-YOUNG, et al. “Arene-Perfluoroarene Interactions in Solution.” Journal of Organic Chemistry, vol. 86, no. 12, Jun. 2021, pp. 8425-8436. https://doi.org/10.1021/acs.joc.1c00921.