Synthesis and complexation properties of "zorbarene": A new naphthalene ring-based molecular receptor

Journal of Organic Chemistry

Volumn 70, Issue 4, 2005, Pages 1115-1121

  Tran, Anh Huu ^a   Miller, David O ^a   Georghiou, Paris E ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; CONFORMATIONS; CRYSTAL STRUCTURE; POSITIVE IONS; SYNTHESIS (CHEMICAL); X RAYS;

ASSOCIATION CONSTANTS; COMPLEXATION PROPERTIES; RING-BASED MACROCYCLES; X-RAY CRYSTAL STRUCTURES;

NAPHTHALENE;

2,3 DIHYDROXYNAPHTHALENE DERIVATIVE; ACETONITRILE; CALIXARENE; CATION; MACROCYCLIC COMPOUND; NAPHTHALENE DERIVATIVE; OCTAHOMOTETRAOXAISOCALIX[4]NAPHTHALENE DERIVATIVE; RECEPTOR; TETRAMETHYLAMMONIUM; UNCLASSIFIED DRUG; ZORBARENE;

ABSORPTION SPECTROSCOPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; CONFORMATION; CRYSTAL STRUCTURE; MOLECULAR MODEL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 13844308335     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0484427     Document Type: Article

References (34)

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2. For other examples of naphthalene-ring based macrocycles see: (a) Shorthill, B. J.; Avetta, C. T.; Glass, T. E. J. Am. Chem. Soc. 2004, 126, 12732. (b) Shorthill, B. J.; Granucci, R. G.; Powell, D. R.; Glass, T. E. J. Org. Chem. 2002, 67, 904.
3. Structure 1 is one of four regioisomers of 1-naphthol-based calix-[4]naphthalenes which were reported in 1993. See: (a) Georghiou, P. E.; Li, Z. Tetrahedron Lett. 1993, 34, 2887. (b) The synthesis of the newest member of the calixnaphthalene family was reported recently: Chowdhury, S.; Georghiou, P. E. J. Org. Chem. 2002, 67, 6808.
4. Structure 1 is one of four regioisomers of 1-naphthol-based calix-[4]naphthalenes which were reported in 1993. See: (a) Georghiou, P. E.; Li, Z. Tetrahedron Lett. 1993, 34, 2887. (b) The synthesis of the newest member of the calixnaphthalene family was reported recently: Chowdhury, S.; Georghiou, P. E. J. Org. Chem. 2002, 67, 6808.
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10. A preliminary account of this work was presented at "Calix 2003", the 7th International Conference on Calixarenes, Vancouver, B.C., Canada, August 19-25, 2003.
11. Molecular modeling was conducted using Spartan Pro V1.1 Molecular Modeling Software from Wavefunction Inc.: Irvine, CA. PM3 calculations were conducted on the optimized geometry of the host and/ or complexes which were obtained through molecular mechanics (MMFF94) conformational searches.
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22. (a) On the basis of the numbering used for the C atoms in the X-ray determination and in the PLUTO plot (see Supporting Information) the naphthyl subunits designated as A to D contain carbon atoms C2-C11; C14-C23; C26-C35; and C38-C47, respectively.
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25. Amusingly, the structure generated by the X-ray crystallography can be imagined to resemble a ring of four anthropomorphic dancers. We propose calling this molecule a "Zorbarene" in honour of the dance-loving "Zorba" character created by the Greek writer Nikos Kazantzakis (1883-1957) in the widely acclaimed and popular book "Zorba the Greek" originally published in 1952. For an account of the origins of various names coined by organic chemists see: Nickon, A.; Silversmith, E. F. Organic Chemistry. The Name Game; Pergamon Books, Inc.: Oxford, U.K., 1987.
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34. Atomic coordinates for the structure of 5b have been deposited with the Cambridge Crystallographic Data Centre. These are available upon request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EK, U.K.