Abstract
The synthesis and full characterization of eight new calix[n]arene sulfonate esters including their conformational analysis were carried out. While p-tBu-calix[6]arene and p-tBu-calix[8]arene esters are conformationally labile in the temperature interval of 25-100°C, p-tBu-calix[4]arene mono- and diesters were isolated as stable conformers at ambient temperature. Two 1,3-functionalised compounds of these derivatives, p-tert-butylcalix[4]arene ditriflate (5) and dimesylate (6) were shown unexpectedly high conformational stability up to 100°C by dynamic NMR measurements. The NMR measurements confirm the pinched-cone conformation for both derivatives. For the dealkylated calix[4]arene derivatives the partial cone conformer of the triesters have been obtained as major products in all cases.
| Original language | English |
|---|---|
| Pages (from-to) | 69-77 |
| Number of pages | 9 |
| Journal | Supramolecular Chemistry |
| Volume | 10 |
| Issue number | 1 |
| Publication status | Published - 1998 |
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Keywords
- 'Pinched cone' conformation
- Calixarene
- NMR
- Sulfonate esters
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Synthetic and NMR studies on calix[n]arene (n = 4,6,8) triflates, mesylates, and tosylates. / Csók, Zsolt; Szalontai, Gábor; Czira, Gábor; Kollár, L.
In: Supramolecular Chemistry, Vol. 10, No. 1, 1998, p. 69-77.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthetic and NMR studies on calix[n]arene (n = 4,6,8) triflates, mesylates, and tosylates
AU - Csók, Zsolt
AU - Szalontai, Gábor
AU - Czira, Gábor
AU - Kollár, L.
PY - 1998
Y1 - 1998
N2 - The synthesis and full characterization of eight new calix[n]arene sulfonate esters including their conformational analysis were carried out. While p-tBu-calix[6]arene and p-tBu-calix[8]arene esters are conformationally labile in the temperature interval of 25-100°C, p-tBu-calix[4]arene mono- and diesters were isolated as stable conformers at ambient temperature. Two 1,3-functionalised compounds of these derivatives, p-tert-butylcalix[4]arene ditriflate (5) and dimesylate (6) were shown unexpectedly high conformational stability up to 100°C by dynamic NMR measurements. The NMR measurements confirm the pinched-cone conformation for both derivatives. For the dealkylated calix[4]arene derivatives the partial cone conformer of the triesters have been obtained as major products in all cases.
AB - The synthesis and full characterization of eight new calix[n]arene sulfonate esters including their conformational analysis were carried out. While p-tBu-calix[6]arene and p-tBu-calix[8]arene esters are conformationally labile in the temperature interval of 25-100°C, p-tBu-calix[4]arene mono- and diesters were isolated as stable conformers at ambient temperature. Two 1,3-functionalised compounds of these derivatives, p-tert-butylcalix[4]arene ditriflate (5) and dimesylate (6) were shown unexpectedly high conformational stability up to 100°C by dynamic NMR measurements. The NMR measurements confirm the pinched-cone conformation for both derivatives. For the dealkylated calix[4]arene derivatives the partial cone conformer of the triesters have been obtained as major products in all cases.
KW - 'Pinched cone' conformation
KW - Calixarene
KW - NMR
KW - Sulfonate esters
UR - http://www.scopus.com/inward/record.url?scp=0032272636&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0032272636&partnerID=8YFLogxK
M3 - Article
VL - 10
SP - 69
EP - 77
JO - Supramolecular Chemistry
JF - Supramolecular Chemistry
SN - 1061-0278
IS - 1
ER -