Abstract
It was found that the "cone" - "partial-cone" equilibrium in 25,26,27,28-tetramethoxycalix[4]arene derivatives is sensitively affected by the solvent polarity: the cone% increases with the increase in the solvent polarity. The novel finding was rationalized in terms of the difference in the dipole moment: cone conformers with four dipole moments orientating into the same direction are more polar than partial-cone conformers with one inverted phenyl unit and therefore are more stabilized in polar solvents. Alkali metal cations such as Li+ and Na+ strongly interact with four methoxy oxygens, resulting in the shift of the equilibrium to cone.
| Original language | English |
|---|---|
| Pages (from-to) | 9937-9946 |
| Number of pages | 10 |
| Journal | Tetrahedron |
| Volume | 49 |
| Issue number | 44 |
| DOIs | |
| Publication status | Published - 1993 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
"Cone" - "Partial-cone" Isomerism in Tetramethoxycalix[4]arenes. Influence of Solvent Polarity and Metal Ions. / Iwamoto, Koji; Ikeda, Atsushi; Araki, Koji; Harada, Takaaki; Shinkai, Seiji.
In: Tetrahedron, Vol. 49, No. 44, 1993, p. 9937-9946.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - "Cone" - "Partial-cone" Isomerism in Tetramethoxycalix[4]arenes. Influence of Solvent Polarity and Metal Ions
AU - Iwamoto, Koji
AU - Ikeda, Atsushi
AU - Araki, Koji
AU - Harada, Takaaki
AU - Shinkai, Seiji
PY - 1993
Y1 - 1993
N2 - It was found that the "cone" - "partial-cone" equilibrium in 25,26,27,28-tetramethoxycalix[4]arene derivatives is sensitively affected by the solvent polarity: the cone% increases with the increase in the solvent polarity. The novel finding was rationalized in terms of the difference in the dipole moment: cone conformers with four dipole moments orientating into the same direction are more polar than partial-cone conformers with one inverted phenyl unit and therefore are more stabilized in polar solvents. Alkali metal cations such as Li+ and Na+ strongly interact with four methoxy oxygens, resulting in the shift of the equilibrium to cone.
AB - It was found that the "cone" - "partial-cone" equilibrium in 25,26,27,28-tetramethoxycalix[4]arene derivatives is sensitively affected by the solvent polarity: the cone% increases with the increase in the solvent polarity. The novel finding was rationalized in terms of the difference in the dipole moment: cone conformers with four dipole moments orientating into the same direction are more polar than partial-cone conformers with one inverted phenyl unit and therefore are more stabilized in polar solvents. Alkali metal cations such as Li+ and Na+ strongly interact with four methoxy oxygens, resulting in the shift of the equilibrium to cone.
UR - http://www.scopus.com/inward/record.url?scp=0027481972&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0027481972&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)80191-5
DO - 10.1016/S0040-4020(01)80191-5
M3 - Article
AN - SCOPUS:0027481972
VL - 49
SP - 9937
EP - 9946
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 44
ER -