Amine guest size and hydrogen-bonding influence the structures of p-tert-butylcalix[4]arene inclusions

作者: Eric B. Brouwer , Kostantin A. Udachin , Gary D. Enright , John A. Ripmeester

DOI: 10.1039/B001274M

关键词:

摘要: A novel structure involving a 2(p-tert-butylcalix[4]arene)·3.5(1,4-butanediamine) inclusion compound shows amine sites both exo and endo to the cavity, with the hydrogen-bonding itself as well host hydroxyl groups; for bulky amines large pKa values, steric factors are more important than basicity, formation of 1∶1, high-symmetry host–guest is preferred over a low-symmetry hydrogen-bonded structure.

参考文章(8)
E. B. Brouwer, G. D. Enright, J. A. Ripmeester, Solid-State NMR and Diffraction Studies of a Tunable p-tert-Butylcalix[4]arene·Guest Structure§ Journal of the American Chemical Society. ,vol. 119, pp. 5404- 5412 ,(1997) , 10.1021/JA9637762
C. David Gutsche, Muzaffar Iqbal, Iftikhar Alam, Calixarenes. 20. The interaction of calixarenes and amines Journal of the American Chemical Society. ,vol. 109, pp. 4314- 4320 ,(1987) , 10.1021/JA00248A029
Teresa Grady, Stephen J. Harris, Malcolm R. Smyth, Dermot Diamond, Perry Hailey, Determination of the Enantiomeric Composition of Chiral Amines Based on the Quenching of the Fluorescence of a Chiral Calixarene Analytical Chemistry. ,vol. 68, pp. 3775- 3782 ,(1996) , 10.1021/AC960383C
Eric B. Brouwer, Gary D. Enright, Christopher I. Ratcliffe, Glenn A. Facey, John A. Ripmeester, Weak Intermolecular Interactions and Molecular Recognition: Structure and Dynamics of the Benzene and Pyridine p-tert-Butylcalix[4]arene Inclusions† Journal of Physical Chemistry B. ,vol. 103, pp. 10604- 10616 ,(1999) , 10.1021/JP9921598
Lorenz J. Bauer, C. David Gutsche, Calixarenes. 15. The formation of complexes of calixarenes with neutral organic molecules in solution Journal of the American Chemical Society. ,vol. 107, pp. 6063- 6069 ,(1985) , 10.1021/JA00307A040
Angela F. Danil de Namor, Robert M. Cleverley, Mariel L. Zapata-Ormachea, Thermodynamics of Calixarene Chemistry. Chemical Reviews. ,vol. 98, pp. 2495- 2526 ,(1998) , 10.1021/CR970095W
G. M. Sheldrick, Phase annealing in SHELX-90: direct methods for larger structures Acta Crystallographica Section A Foundations of Crystallography. ,vol. 46, pp. 467- 473 ,(1990) , 10.1107/S0108767390000277
Angela F. Danil de Namor, Maria T. Garrido Pardo, David A. Pacheco Tanaka, Felix J. Sueros Velarde, Jaime D. Cárdenas García, Mercedes C. Cabaleiro, Jasim M. A. Al-Rawi, From neutral to ionic species: amine–p-tert-butylcalix(n)arene (n= 6, 8) interaction. Electrochemical, thermodynamic and structural studies in benzonitrile Journal of the Chemical Society, Faraday Transactions. ,vol. 89, pp. 2727- 2736 ,(1993) , 10.1039/FT9938902727