The saddle form of cyclotriveratrylene
Publication type: Journal Article
Publication date: 2004-11-06
scimago Q1
wos Q3
SJR: 0.742
CiteScore: 5.3
Impact factor: 2.9
ISSN: 15206106, 15205207, 10895647
Materials Chemistry
Surfaces, Coatings and Films
Physical and Theoretical Chemistry
Abstract
Cyclotriveratrylene (CTV), or hexamethoxy tribenzocyclononatriene (hexamethoxy-TBCN) and other peripherally hexa-(or tri-)substituted TBCN were so far only known to exist in their crown form. Attempts to detect the corresponding saddle isomers failed, even though when structurally chiral these compounds undergo racemization, a process that is believed to proceed via the saddle form. We show that the saddle form of CTV (and other peripherally hexa-substituted TBCN) can be obtained by rapidly quenching a hot solution or the high-temperature melt to below room temperature. The saddle form of CTV was quantitatively separated from the quenched material by column chromatography, and some of its thermodynamic and kinetic properties in solution and in the solid state were determined by proton and carbon-13 NMR. Detailed measurement were performed in chloroform solutions, for which it was found that at room temperature the equilibrium constant, K = [saddle]/[crown] = exp[−(ΔH − TΔS)/RT, is ∼0.1 (with ΔH = 9.96 ± 0...
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54
Total citations:
54
Citations from 2025:
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(3.7%)
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GOST
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Zimmermann H. et al. The saddle form of cyclotriveratrylene // Journal of Physical Chemistry B. 2004. Vol. 108. No. 48. pp. 18772-18778.
GOST all authors (up to 50)
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Zimmermann H., Tolstoy P. M., LIMBACH H. G., Poupko R., Luz Z. The saddle form of cyclotriveratrylene // Journal of Physical Chemistry B. 2004. Vol. 108. No. 48. pp. 18772-18778.
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RIS
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TY - JOUR
DO - 10.1021/jp040482r
UR - https://doi.org/10.1021/jp040482r
TI - The saddle form of cyclotriveratrylene
T2 - Journal of Physical Chemistry B
AU - Zimmermann, Herbert
AU - Tolstoy, Peter M.
AU - LIMBACH, H. G.
AU - Poupko, Raphy
AU - Luz, Zeev
PY - 2004
DA - 2004/11/06
PB - American Chemical Society (ACS)
SP - 18772-18778
IS - 48
VL - 108
SN - 1520-6106
SN - 1520-5207
SN - 1089-5647
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2004_Zimmermann,
author = {Herbert Zimmermann and Peter M. Tolstoy and H. G. LIMBACH and Raphy Poupko and Zeev Luz},
title = {The saddle form of cyclotriveratrylene},
journal = {Journal of Physical Chemistry B},
year = {2004},
volume = {108},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/jp040482r},
number = {48},
pages = {18772--18778},
doi = {10.1021/jp040482r}
}
Cite this
MLA
Copy
Zimmermann, Herbert, et al. “The saddle form of cyclotriveratrylene.” Journal of Physical Chemistry B, vol. 108, no. 48, Nov. 2004, pp. 18772-18778. https://doi.org/10.1021/jp040482r.
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