On the nature of arene η6 interactions in the solid state and the use of cylindrophanes as ligands for sandwich complexation of metals with longer- range interactions with the benzene ring

European Journal of Inorganic Chemistry

Volumn , Issue 3, 2000, Pages 485-490

  Mascal, Mark ^a   Kerdelhué, Jean Luc ^a   Blake, Alexander J ^a   Cooke, Paul A ^a   Mortimer, Roger J ^b   Teat, Simon J ^c  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^c DARESBURY LABORATORY   (United Kingdom)

Author keywords

Coordination modes; Cyclophanes; Macrocycles; Sandwich complexes; Solid state structures

Indexed keywords

BENZENE; COMPLEXATION; COPPER COMPOUNDS; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SILVER COMPOUNDS;

AS-LIGANDS; BENZENE RING; COORDINATION MODES; CYCLOPHANES; LONG RANGE INTERACTIONS; LONGER-RANGE INTERACTION; MACROCYCLES; METALS IONS; SANDWICH COMPLEXES; SOLID-STATE STRUCTURES;

METAL IONS;

BENZENE DERIVATIVE; BORON DERIVATIVE; COORDINATION COMPOUND; COPPER DERIVATIVE; CYCLOPHANE; FLUORINE DERIVATIVE; METAL COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON; SILVER DERIVATIVE;

ARTICLE; CHEMICAL BOND; COMPLEX FORMATION; CRYSTAL STRUCTURE; ISOMERISM; LIGAND BINDING; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE;

EID: 0034048706     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0682(200003)2000:3<485::aid-ejic485>3.0.co;2-r     Document Type: Article

References (27)

1. 6-complexes have been prepared (see F. G. N. Cloke, Chem. Soc. Rev. 1993, 22, 17-24), but do not appear in the present study since no X-ray crystal structures have been published.
2. M. Mascal, J.-L. Kerdelhué, A. J. Blake, P. A. Cooke, Angew. Chem. 1999. 111, 2094-2096; Angew. Chem. Int. Ed. 1999, 38, 1968-1971.
3. M. Mascal, J.-L. Kerdelhué, A. J. Blake, P. A. Cooke, Angew. Chem. 1999. 111, 2094-2096; Angew. Chem. Int. Ed. 1999, 38, 1968-1971.
4. The term "macrobicycle" as applied here is used as an analogy to cryptand macrobicycles with aromatic rings counted as bridgeheads, and is not intended to be a formal description of the ring system.
5. J. Hansen, A. J. Blake, W.-S. Li, M. Mascal, J. Chem. Soc., Perkin Trans, 1 1998, 3371-3376.
6. A. G. Orpen, L. Brammer, F. H. Allen, O. Kennard, D. G. Watson, R. Taylor, J. Chem. Soc., Dalton Trans. 1989, S1-S83.
7. [6a] O. Kennard, F. H. Allen, Chem. Des. Autom. News 1993, 8, 31-37. -
8. [6b] D. A. Fletcher, R. F. McMeeking, D. Parkin, J. Chem. Inf. Comput. Sci. 1996, 36, 746-749.
9. Van der Waals radjus values for metals vary between 1.39 Å for zinc and 2.75 A for potassium: A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
10. B. P. Pozniak, R. C. Dunbar, J. Am. Chem. Soc. 1997, 119, 10439-10445 and references therein.
11. A generic Van der Waals cutoff limit of om < 3.6 Å applies to all longer-range contacts. Over 80% of the observations in this range involve intermolecular metal-arene contact, which mitigates against proximity imposed by bonded, intramolecular relationships between the metal and the ring.
12. H. Schmidbaur, Angew. Chem. 1985, 97, 893-904; Angew. Chem. Int. Ed. Engl. 1985, 24, 893-904.
13. H. Schmidbaur, Angew. Chem. 1985, 97, 893-904; Angew. Chem. Int. Ed. Engl. 1985, 24, 893-904.
14. J. L. Atwood, W. E. Hunter, R. D. Rogers, J. A. Weeks, J. Inclusion Phenom. 1985, 3, 113-123.
15. [12a] A. Ikeda, H. Tsuzuki, S. Shinkai, Tetrahedron Lett. 1994, 35, 8417-8420. -
16. [12b] P. D. Beer, M. G. B. Drew, P. A. Gale, P. B. Leeson, M. I. Ogden, J. Chem. Soc., Dalton Trans. 1994, 3479-3485. -
17. [12c] X. Delaigue, M. W. Hosseini, N. Kyritsakas, A. de Cian, J. Fischer, J. Chem. Soc., Chem. Commun. 1995. 609-610.
18. F. Fages, J.-P. Desvergne, H. Bouas-Laurent, J. Hinschberger, P. Marsau, M. Petraud, New J. Chem. 1988, 12, 95-106.
19. H. Andrianatoadndro, Y. Barrans, P. Marsau, J. P. Desvergne, F. Fages, H. Bouas-Laurent, Acta Crystallogr., Sect. B 1995, 57, 293-300.
20. C. M. Hartshorn, P. J. Steel, Angew. Chem. 1996, 108, 2818-2820;
21. Angew. Chem. Int. Ed. Engl. 1996, 35, 2655-2657.
22. Molecular mechanics simulations performed with MACROMODEL version 5.5 with the MM2 force field: F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still J. Comp. Chem. 1990, 11, 440-467.
23. Full data for the crystal stucture determinations is given in reference 2.
24. II.
25. For example: M. Pasquali, C. Floriani, A. Gaetani-Manfredotti, Inorg. Chem. 1980, 19, 1191-1197.
26. 2 bonding will be the subject of a separate report (in preparation). See also K. Shelly, D. C. Finster, Y. J. Lee, W. R. Scheidt, C. A. Reed, J. Am. Chem. Soc. 1985, 107, 5955-5959.
27. 1 sandwich has been described: J. D. Ferrara, A. Djebli, C. Tessier-Youngs, W. J. Youngs, J. Am. Chem. Soc. 1988, 119, 647-649.