Complex formation between 1-chloro-4-(trifluoromethyl)benzene (guest) and 4-tert-butylcalix[4]arenes (host) distally substituted with phosphonic acid or phosphonic ester groups at the lower rim

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Abstract

The complexation behavior of the distally substituted phosphonic acid and phosphonic ester 4-tert-butylcalix[4]arenes (hosts) with 1-chloro-4-(trifluoromethyl)benzene (guest) was examined in chloroform. The complex stability constants (Ks) and the thermodynamic parameters of the complexation were determined by a spectrofluorometric method using Job's method and van't Hoff theory, respectively. A strong dependence of the host-guest interaction on the extent of distortion in the conformation of calixarene host cavity was obtained. The 'pinched cone' conformer of 1,3-substituted calix[4]arenes seems to form a complex with electron-deficient neutral aromatics predominantly through π-π type interaction.

Original languageEnglish
Pages (from-to)5119-5124
Number of pages6
JournalTetrahedron
Volume58
Issue number25
DOIs
Publication statusPublished - Jun 17 2002

Fingerprint

Complexation
Esters
Calixarenes
Organophosphonates
Chloroform
Thermodynamics
Conformations
Cones
Electrons
1-chloro-4-(trifluoromethyl)benzene
phosphonic acid

Keywords

  • Calixarenes
  • Complex stability
  • Neutral guest
  • Recognition

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Complex formation between 1-chloro-4-(trifluoromethyl)benzene (guest) and 4-tert-butylcalix[4]arenes (host) distally substituted with phosphonic acid or phosphonic ester groups at the lower rim",
abstract = "The complexation behavior of the distally substituted phosphonic acid and phosphonic ester 4-tert-butylcalix[4]arenes (hosts) with 1-chloro-4-(trifluoromethyl)benzene (guest) was examined in chloroform. The complex stability constants (Ks) and the thermodynamic parameters of the complexation were determined by a spectrofluorometric method using Job's method and van't Hoff theory, respectively. A strong dependence of the host-guest interaction on the extent of distortion in the conformation of calixarene host cavity was obtained. The 'pinched cone' conformer of 1,3-substituted calix[4]arenes seems to form a complex with electron-deficient neutral aromatics predominantly through π-π type interaction.",
keywords = "Calixarenes, Complex stability, Neutral guest, Recognition",
author = "S. Kuns{\'a}gi-M{\'a}t{\'e} and G. Nagy and Petr Jurecka and L. Koll{\'a}r",
year = "2002",
month = "6",
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language = "English",
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pages = "5119--5124",
journal = "Tetrahedron",
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publisher = "Elsevier Limited",
number = "25",

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TY - JOUR

T1 - Complex formation between 1-chloro-4-(trifluoromethyl)benzene (guest) and 4-tert-butylcalix[4]arenes (host) distally substituted with phosphonic acid or phosphonic ester groups at the lower rim

AU - Kunsági-Máté, S.

AU - Nagy, G.

AU - Jurecka, Petr

AU - Kollár, L.

PY - 2002/6/17

Y1 - 2002/6/17

N2 - The complexation behavior of the distally substituted phosphonic acid and phosphonic ester 4-tert-butylcalix[4]arenes (hosts) with 1-chloro-4-(trifluoromethyl)benzene (guest) was examined in chloroform. The complex stability constants (Ks) and the thermodynamic parameters of the complexation were determined by a spectrofluorometric method using Job's method and van't Hoff theory, respectively. A strong dependence of the host-guest interaction on the extent of distortion in the conformation of calixarene host cavity was obtained. The 'pinched cone' conformer of 1,3-substituted calix[4]arenes seems to form a complex with electron-deficient neutral aromatics predominantly through π-π type interaction.

AB - The complexation behavior of the distally substituted phosphonic acid and phosphonic ester 4-tert-butylcalix[4]arenes (hosts) with 1-chloro-4-(trifluoromethyl)benzene (guest) was examined in chloroform. The complex stability constants (Ks) and the thermodynamic parameters of the complexation were determined by a spectrofluorometric method using Job's method and van't Hoff theory, respectively. A strong dependence of the host-guest interaction on the extent of distortion in the conformation of calixarene host cavity was obtained. The 'pinched cone' conformer of 1,3-substituted calix[4]arenes seems to form a complex with electron-deficient neutral aromatics predominantly through π-π type interaction.

KW - Calixarenes

KW - Complex stability

KW - Neutral guest

KW - Recognition

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U2 - 10.1016/S0040-4020(02)00474-X

DO - 10.1016/S0040-4020(02)00474-X

M3 - Article

VL - 58

SP - 5119

EP - 5124

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 25

ER -