Ethylammonium Nitrate (EAN)/Tf2O and EAN/TFAA: Ionic Liquid Based Systems for Aromatic Nitration
1
Department of Chemistry, University of North Florida, 1 UNF Drive, Jacksonville, Florida 32224, United States
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Publication type: Journal Article
Publication date: 2011-09-13
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
21861464
Organic Chemistry
Abstract
Acting as in situ sources of triflyl nitrate (TfONO(2)) and trifluoroacetyl nitrate (CF(3)COONO(2)), the EAN/Tf(2)O and EAN/TFAA systems, generated via metathesis in the readily available ethylammonium nitrate (EAN) ionic liquid as solvent, are powerful electrophilic nitrating reagents for a wide variety of aromatic and heteroaromatic compounds. Comparative nitration experiments indicate that EAN/Tf(2)O is superior to EAN/TFAA for nitration of strongly deactivated systems. Both systems exhibit low substrate selectivity (K(T)/K(B) = 5-10) in between values reported for covalent nitrates and preformed nitronium salts.
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Citations from 2025:
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GOST
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Aridoss G., Laali K. K. Ethylammonium Nitrate (EAN)/Tf2O and EAN/TFAA: Ionic Liquid Based Systems for Aromatic Nitration // Journal of Organic Chemistry. 2011. Vol. 76. No. 19. pp. 8088-8094.
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Aridoss G., Laali K. K. Ethylammonium Nitrate (EAN)/Tf2O and EAN/TFAA: Ionic Liquid Based Systems for Aromatic Nitration // Journal of Organic Chemistry. 2011. Vol. 76. No. 19. pp. 8088-8094.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo201374a
UR - https://doi.org/10.1021/jo201374a
TI - Ethylammonium Nitrate (EAN)/Tf2O and EAN/TFAA: Ionic Liquid Based Systems for Aromatic Nitration
T2 - Journal of Organic Chemistry
AU - Aridoss, Gopalakrishnan
AU - Laali, Kenneth K
PY - 2011
DA - 2011/09/13
PB - American Chemical Society (ACS)
SP - 8088-8094
IS - 19
VL - 76
PMID - 21861464
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2011_Aridoss,
author = {Gopalakrishnan Aridoss and Kenneth K Laali},
title = {Ethylammonium Nitrate (EAN)/Tf2O and EAN/TFAA: Ionic Liquid Based Systems for Aromatic Nitration},
journal = {Journal of Organic Chemistry},
year = {2011},
volume = {76},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/jo201374a},
number = {19},
pages = {8088--8094},
doi = {10.1021/jo201374a}
}
Cite this
MLA
Copy
Aridoss, Gopalakrishnan, and Kenneth K Laali. “Ethylammonium Nitrate (EAN)/Tf2O and EAN/TFAA: Ionic Liquid Based Systems for Aromatic Nitration.” Journal of Organic Chemistry, vol. 76, no. 19, Sep. 2011, pp. 8088-8094. https://doi.org/10.1021/jo201374a.