Structural Comparisons of the Binding Cores Formed by 1,3-di-Amide Derivatives of p-tert-Butylcalix[4] arene: Arms Stabilization through Intra-molecular Interactions Including N-H center dot center dot center dot O, O-H center dot center dot center dot Cl and pi center dot center dot center dot Cl Types
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Title |
Structural Comparisons of the Binding Cores Formed by 1,3-di-Amide Derivatives of p-tert-Butylcalix[4] arene: Arms Stabilization through Intra-molecular Interactions Including N-H center dot center dot center dot O, O-H center dot center dot center dot Cl and pi center dot center dot center dot Cl Types
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Creator |
DEY, M
GUIONNEAU, P HINGE, VK RAO, CP |
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Subject |
p-tert-Butyl calix[4] arene
1,3-di-Amide derivative Single crystal X-ray diffraction Molecular recognition Intramolecular hydrogen bond CRYSTAL-STRUCTURES SELECTIVE RECOGNITION HG2+ ION |
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Description |
This paper deals with the development of a receptor with selectively functionalized at the lower rim of p-tert-butyl calix[4] arene linked through amide bond, resulting in the diamide derivatives (L-1, L-2 and L-3) suitable for sensing ions and molecules. All the derivatives were thoroughly characterized by analytical and spectral methods. These derivatives were structurally characterized by single crystal X-ray diffraction and the conformational features of the calix[4] arene as well as the pendants are discussed. The L-1 and L-2 exhibited intramolecular hydrogen bond interaction between the N-H and the lower rim phenolic oxygen in addition to the circular hydrogen bonding between the phenolic O-H and the ether oxygen of the adjacent strand. The corresponding H-bond is absent when no 'H' is present on amide-N as in case of L-3. Such intramolecular N-H center dot center dot center dot O interactions observed with the pendant results in a conformational bend responsible for the orientation of the arms and there by the nature of the binding core formed. Thus the binding cores formed differ largely between L-3 and the other two.
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Publisher |
NATL ACAD SCIENCES INDIA
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Date |
2014-12-29T04:55:46Z
2014-12-29T04:55:46Z 2014 |
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Type |
Article
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Identifier |
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES INDIA SECTION A-PHYSICAL SCIENCES, 84(2)297-303
0369-8203 2250-1762 http://dx.doi.org/10.1007/s40010-014-0145-5 http://dspace.library.iitb.ac.in/jspui/handle/100/17130 |
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Language |
English
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