The Antiaromatic Nucleophilic Substitution Reaction (SNAAr) in Cycloheptatrienyl-Anion Containing Zwitterions with a Möbius-Aromatic Intermediate
Alena D Sokolova
1
,
Dmitry N Platonov
1
,
Dmitry Platonov
1
,
Alexander Yu Belyy
1
,
Rinat F Salikov
1
,
Kirill S Erokhin
1
,
Publication type: Journal Article
Publication date: 2024-07-03
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
38958743
Abstract
Antiaromatic nucleophilic substitution reactions in cycloheptatrienide pyridinium and phosphonium zwitterions with initial formation of a cycloheptatetraene intermediate are explored. The mechanism was supported by quantum chemical calculations, first-order reaction kinetics, and high-resolution mass spectrometry. The pyridinium zwitterion exhibited weak antiaromaticity, whereas the intermediate displayed Möbius aromaticity, as evidenced by nuclear independent chemical shift values and the shape of its HOMO. This study represents the eighth confirmed instance of a Möbius-aromatic organic species in its ground state.
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Sokolova A. D. et al. The Antiaromatic Nucleophilic Substitution Reaction (SNAAr) in Cycloheptatrienyl-Anion Containing Zwitterions with a Möbius-Aromatic Intermediate // Organic Letters. 2024. Vol. 26. No. 28. pp. 5877-5882.
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Sokolova A. D., Platonov D. N., Platonov D., Belyy A. Yu., Salikov R. F., Erokhin K. S., Tomilov Y. V. The Antiaromatic Nucleophilic Substitution Reaction (SNAAr) in Cycloheptatrienyl-Anion Containing Zwitterions with a Möbius-Aromatic Intermediate // Organic Letters. 2024. Vol. 26. No. 28. pp. 5877-5882.
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TY - JOUR
DO - 10.1021/acs.orglett.4c01446
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.4c01446
TI - The Antiaromatic Nucleophilic Substitution Reaction (SNAAr) in Cycloheptatrienyl-Anion Containing Zwitterions with a Möbius-Aromatic Intermediate
T2 - Organic Letters
AU - Sokolova, Alena D
AU - Platonov, Dmitry N
AU - Platonov, Dmitry
AU - Belyy, Alexander Yu
AU - Salikov, Rinat F
AU - Erokhin, Kirill S
AU - Tomilov, Yury V.
PY - 2024
DA - 2024/07/03
PB - American Chemical Society (ACS)
SP - 5877-5882
IS - 28
VL - 26
PMID - 38958743
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2024_Sokolova,
author = {Alena D Sokolova and Dmitry N Platonov and Dmitry Platonov and Alexander Yu Belyy and Rinat F Salikov and Kirill S Erokhin and Yury V. Tomilov},
title = {The Antiaromatic Nucleophilic Substitution Reaction (SNAAr) in Cycloheptatrienyl-Anion Containing Zwitterions with a Möbius-Aromatic Intermediate},
journal = {Organic Letters},
year = {2024},
volume = {26},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c01446},
number = {28},
pages = {5877--5882},
doi = {10.1021/acs.orglett.4c01446}
}
Cite this
MLA
Copy
Sokolova, Alena D., et al. “The Antiaromatic Nucleophilic Substitution Reaction (SNAAr) in Cycloheptatrienyl-Anion Containing Zwitterions with a Möbius-Aromatic Intermediate.” Organic Letters, vol. 26, no. 28, Jul. 2024, pp. 5877-5882. https://pubs.acs.org/doi/10.1021/acs.orglett.4c01446.