Synthesis and host-guest properties of a calix[6]arene based receptor closed by an internal ion-paired cap

Tetrahedron Letters

Volumn 49, Issue 24, 2008, Pages 3848-3852

  Richard, Jean Alexandre ^a   Pamart, Marc ^b   Hucher, Nicolas ^a   Jabin, Ivan ^b  

^a UNIVERSITÉ DU HAVRE   (France)

^b UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

Author keywords

Ammonium ion; Calixarenes; Host guest chemistry; Molecular recognition; Supramolecular chemistry

Indexed keywords

AMMONIA; CALIXARENE; CARBOXYLIC ACID; ION; RECEPTOR;

ARTICLE; BINDING SITE; CHEMICAL BINDING; CONFORMATION; ENCAPSULATION; HYDROGEN BOND; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 43049161018     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.085     Document Type: Article

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41. 2), 124.4, 124.6, 124.7, 125.5, 125.8, 126.1, 126.1(6), 126.8, 127.0, 127.2, 127.4, 128.0, 128.6, 132.3, 132.7, 132.8, 133.4, 133.7, 134.0, 142.0, 145.8, 146.0, 146.9, 151.0, 152.2, 153.7, 154.4.
42. 2O: C, 76.22; H, 8.75; N, 1.02. Found: C, 76.13; H, 8.78; N, 1.02.
43. +) 1493.90; found 1493.73.
44. 2O: C, 77.83; H, 8.49; N, 1.01. Found: C, 78.18; H, 8.73; N, 1.05.
45. +) 1314.7973; found 1314.7970.
46. CH2 Br = 2.34 ppm.
47. OMe = 2.72 ppm.
48. OCH2 CO = 4.57 and 3.60 ppm for 6 and 7·HCl, respectively, (determined by HMQC analysis).
49. CH 3 = - 1.56 ppm). This result confirms that the deprotonation of the COOH groups of the host is required, highlighting the importance of ion-pair interactions in the recognition process.
50. Such CH-π interactions have been observed in closely related host-guest complexes, see Ref. 11.