Noncovalent assembly of functional groups on calix[4]arene molecular boxes

Chemistry - A European Journal

Volumn 3, Issue 11, 1997, Pages 1823-1832

  Timmerman, Peter ^a   Vreekamp, Remko H ^a   Hulst, Ron ^a   Verboom, Willem ^a   Reinhoudt, David N ^a   Rissanen, Kari ^b   Udachin, Konstantin A ^c   Ripmeester, John ^c  

^a UNIVERSITY OF TWENTE   (Netherlands)

^b UNIVERSITY OF JYVÄSKYLÄ   (Finland)

^c NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

Calixarenes; Hydrogen bonds; Molecular boxes; Noncovalent assembly; Supramolecular chemistry

Indexed keywords

EID: 0030733209     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970031115     Document Type: Article

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44. "Pinched" means that two opposite aromatic rings become parallel, while the other two twist outward and "flatten" the calixarene.
45. Two X-ray crystal structures from single rosette assemblies have been reported so far: a) J. P. Mathias, E. E. Simanek, J. A. Zerkowski, C. T. Seto, G. M. Whitesides, J. Am. Chem. Soc. 1994, 116, 4316-4325: b) M. Mascal, N. M. Hecht, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2348-2350; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204-2206.
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47. Two X-ray crystal structures from single rosette assemblies have been reported so far: a) J. P. Mathias, E. E. Simanek, J. A. Zerkowski, C. T. Seto, G. M. Whitesides, J. Am. Chem. Soc. 1994, 116, 4316-4325: b) M. Mascal, N. M. Hecht, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2348-2350; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204-2206.
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51. Mass spectrometric evidence for noncovalent rosette assemblies has so far only been obtained with ESMS : a) K. C. Russell, E. Leize, A. Van Dorsselaer. J.-M. Lehn, Angew. Chem. 1995, 107, 244-248; Angew. Chem. Int. Ed. Engl. 1995, 34, 209-213; b) X. Cheng, Q. Gao, R. D. Smith, E. E. Simanek, M. Mammen, G. M. Whitesides, J. Org. Chem. 1996, 61, 2204-2206.
52. Mass spectrometric evidence for noncovalent rosette assemblies has so far only been obtained with ESMS : a) K. C. Russell, E. Leize, A. Van Dorsselaer. J.-M. Lehn, Angew. Chem. 1995, 107, 244-248; Angew. Chem. Int. Ed. Engl. 1995, 34, 209-213; b) X. Cheng, Q. Gao, R. D. Smith, E. E. Simanek, M. Mammen, G. M. Whitesides, J. Org. Chem. 1996, 61, 2204-2206.
53. 3COO led to complete destruction of the box-like assembly.
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55. The minimized gas-phase structure of 4 shows a 2.3 Å hydrogen bond between the p-amino group and the melamine NH protons. The minimized gas-phase structure of 5 gives a much shorter hydrogen bond of 1.9 Å between the amide carbonyl group and the melamine NH protons.
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