A facile, moisture-insensitive method for synthesis of pillar[5]arenes—the solvent templation by halogen bonds
Publication type: Journal Article
Publication date: 2012-11-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A new, very efficient, and selective preparation method of peralkylated pillar[5]arenes is presented. By replacing typical Lewis acids with trifluoroacetic acid (TFA) we were able to eliminate the need of anhydrous conditions without a loss of effectiveness. The method is highly practical: a) it is moisture-insensitive, b) starting from simple and cheap reagents and reactants, and c) allows for chromatography-free isolation of the products. The results indicate that the interactions with solvent molecules can modulate stability of the products and influence the reaction outcome. Dichloromethane (DCM) and dichloroethane (DCE) are complexed within the cyclopentamer cavity with association constants of 120 M−1 and 600 M−1, respectively (CDCl3). The interactions involve a combination of hydrogen–pi and halogen–pi bonds.
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75
Total citations:
75
Citations from 2024:
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(16%)
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GOST
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Boinski T., Szumna A. A facile, moisture-insensitive method for synthesis of pillar[5]arenes—the solvent templation by halogen bonds // Tetrahedron. 2012. Vol. 68. No. 46. pp. 9419-9422.
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Boinski T., Szumna A. A facile, moisture-insensitive method for synthesis of pillar[5]arenes—the solvent templation by halogen bonds // Tetrahedron. 2012. Vol. 68. No. 46. pp. 9419-9422.
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RIS
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TY - JOUR
DO - 10.1016/j.tet.2012.09.006
UR - https://doi.org/10.1016/j.tet.2012.09.006
TI - A facile, moisture-insensitive method for synthesis of pillar[5]arenes—the solvent templation by halogen bonds
T2 - Tetrahedron
AU - Boinski, Tomasz
AU - Szumna, Agnieszka
PY - 2012
DA - 2012/11/01
PB - Elsevier
SP - 9419-9422
IS - 46
VL - 68
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
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@article{2012_Boinski,
author = {Tomasz Boinski and Agnieszka Szumna},
title = {A facile, moisture-insensitive method for synthesis of pillar[5]arenes—the solvent templation by halogen bonds},
journal = {Tetrahedron},
year = {2012},
volume = {68},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/j.tet.2012.09.006},
number = {46},
pages = {9419--9422},
doi = {10.1016/j.tet.2012.09.006}
}
Cite this
MLA
Copy
Boinski, Tomasz, and Agnieszka Szumna. “A facile, moisture-insensitive method for synthesis of pillar[5]arenes—the solvent templation by halogen bonds.” Tetrahedron, vol. 68, no. 46, Nov. 2012, pp. 9419-9422. https://doi.org/10.1016/j.tet.2012.09.006.