peri-interactions in naphthalenes, 16.¹ An expedition into the borderland between molecular and supramolecular chemistry

References

• 15th Communication: Schiemenz, G. P.; Phosphorus, Sulfur, Silicon Relat. Elements 2009, 184, 2247-2262.
   Web of Science ®Google Scholar
• Swiegers, G. F.; Malefetse, T. J. Chem. Rev. 2000, 100, 3483-3537.
   PubMed Web of Science ®Google Scholar
• Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem. 2001, 113, 2446-2492, Angew. Chem., Int. Ed. 2001, 40, 2382-2426. cf. Badjić, J. D.; Nelson, A.; Cantrill, S. J.; Turnbull, W. B.; Stoddart, J. F. Acc. Chem. Res. 2005, 38, 723-732.
   Google Scholar
• Stang, P. J.; Olenyuk, B. Acc. Chem. Res. 1997, 30, 502-518.
   Web of Science ®Google Scholar
• Holliday, B. J.; Mirkin, C. A. Angew. Chem. 2001, 113, 2076-2098, Angew. Chem., Int. Ed. 2001, 40, 2022-2043.
   Google Scholar
• Pauling, L. The Nature of the Chemical Bond, 2nd ed., Cornell University Press: Ithaca NY, London, Oxford 1945 ( 5th printing 1947), p. 53. The revised figures in the 3rd edition (Cornell University Press, Ithaca NY, London, Oxford 1960 ( 12th printing 1993), p. 85) differ significantly, but inconsistently (C-C +42%, C-N +43%, C-O +20%, N-N +92%, P-P +171%, As-As +113%, O-O −5%, O-H +0.4%, F-H −9%, Cl-H +0.5%, Br-H +0.2%, I-H ±0%) and thus indicate that Pauling's bond energies are only rough estimates. The argument is not affected by the revision of the original scale.
   Google Scholar
• Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 509-518. Ward, M. D. Ann. Rep. Progr. Chem., Sect. A, 2000, 96, 345-385, defined that “supramolecular chemistry according to Lehn… is the chemistry of the non-covalent bond… Strictly speaking this definition also includes metal-ligand coordinate bonds.” For pragmatic reasons, Ward assigned metal complexes to the realm of supramolecular chemistry only if “particularly unusual or elaborate molecular architectures” are being formed. While the phrasing “molecular architectures” is at variance with “supramolecular entity,” Ward leaves no doubt that he did not intend to associate the “metal–ligand coordinate bonds” with covalent bonds.
   Web of Science ®Google Scholar
• Staab, H. A. Einführung in die theoretische organische Chemie, Verlag Chemie: Weinheim, 1959, pp. 166-173.
   Google Scholar
• Pauling,6 2nd ed. p. 52, 3rd ed. p. 83.
   Google Scholar
• Christen, H. R. Chemie. Atommodelle Periodensystem Chemische Bindung, Diesterweg·Salle/Verlag Sauerländer, Frankfurt, Berlin, München, Aarau 1972, p. 99.
   Google Scholar
• Jones, C. J. Chem. Soc. Rev. 1998, 27, 289-299.
   Web of Science ®Google Scholar
• Bamberger, E.; Rising, A. Ber. Dtsch. Chem. Ges. 1901, 34, 3877-3880; Lüttke, W. Z. Elektrochem. Ber. Bunsenges. Phys. Chem. 1957, 61, 302-313, 976–986; Gowenlock, B. G.; Lüttke, W. Quart. Rev. 1958, 12, 321-340. Crystal structure: Dieterich, D. A.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1974, 96, 6372-6380.
   Google Scholar
• Schröder, G.; Oth, J. F. M.; Merényi, R. Angew. Chem. 1965, 77, 774-784, Angew. Chem., Int. Ed. Engl. 1965, 4, 752; Schröder, G.; Oth, J. F. M. Angew. Chem. 1967, 79, 458-467, Angew. Chem., Int. Ed. Engl. 1967, 6, 414-423.
   Google Scholar
• Hibbert, F. J. Chem. Soc., Chem. Commun. 1973, 463; Hibbert, F. J. Chem. Soc., Perkin Trans. 2. 1974, 1862-1866; Hibbert, F.; Hunte, K. P. P. J. Chem. Soc., Perkin Trans. 2. 1981, 1562-1565, 1983, 1895-1899; Awwal, A.; Burt, R.; Kresge, A. J. J. Chem. Soc., Perkin Trans. 1981, 2, 1566-1571.
   Google Scholar
• Busch, D. H.; Vance, A. L.; Kolchinski, A. G. In: Sauvage, J.-P.; Hosseini, M. W. (Eds.); Templating, Self-Assembly, and Self-Organization [ Lehn, J.-M.; Comprehensive Supramolecular Chemistry, 9], Pergamon Press: Oxford, 1996; pp. 1-42. For the recent template assisted synthesis of a nine-membered triphosphorus macrocycle, see: Albers, T.; Edwards, P. G. Chem. Commun. 2007, 858-860.
   Google Scholar
• Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401. Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260, aware of the difficulties of giving a satisfactory definition of the term self-assembly and of its liberal use in the literature, proposed to “define self-assembly as a highly convergent synthesis protocol, one that is exclusively driven by noncovalent interactions.” This restriction to noncovalent interactions presupposes a definition which attractive interactions are covalent and which noncovalent. The authors defined N→transition metal bonds as “coordinate covalent bonds (‘dative’ bonds)”, and yet discuss them under the headline “self-assembling supramolecular complexes.” Fyfe and Stoddart, loc. cit., defined self-assembly as “the spontaneous generation of well-definded supramolecular and molecular architectures from specifically ‘engineered’ building blocks.”
   Web of Science ®Google Scholar
• Fujita, M.; Yazaki, J.; Ogura, K. J. Am. Chem. Soc. 1990, 112, 5645-5647.
   Web of Science ®Google Scholar
• Fujita, M.; Yazaki, J.; Ogura, K. Chem. Lett. 1991, 1031-1032; Fujita, M.; Ibukuro, F.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 4175-4176.
   Web of Science ®Google Scholar
• 1a,b form in the reaction of 2,2′-bipyridine with L2Pd/Pt(ONO2)2 in which NO3− ions are generated. Hence, the formation of 1a may, in fact, be template-assisted, too, but proceeds under much milder conditions than that of 1b; the beneficial effect of 2,2′-bipyridinium dinitrate instead of 2,2′-bipyridine in the synthesis of the latter may be due to the higher concentration of NO3−.
   Google Scholar
• Fujita, M.; Oguro, D.; Miyazawa, M.; Oka, H.; Yamaguchi, K.; Ogura, K. Nature 1995, 378, 469-471; Ibukuro, F.; Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 1998, 120, 8561-8562.
   Web of Science ®Google Scholar
• Butlerow, A. Ann. Chem. Pharm 1860, 115, 322-327; Hofmann, A. W. Ber. Dtsch. Chem. Ges. 1869, 2, 152-159; Duden, P.; Scharff, M. Liebigs Ann. Chem. 1895, 288, 218-252; Dickinson, R. G.; Raymond, A. L. J. Am. Chem. Soc. 1923, 45, 22-29. Lindsey, J. S. New J. Chem. 1991, 15, 153-180, focussing on “self-assembly of covalent structures”, “self-assembly with covalent bond formation… under gentle conditions in a single flask procedure”, defined “covalent self-assembly can meet the criteria of strict self-assembly as long as the covalent bonds are reversible… strict self-assembly adheres to the principles of equilibrium thermodynamics.”
   Google Scholar
• Similar contradictions in Janzen, D. E.; Patel, K. N.; VanDerveer, D. G.; Grant, G. J. Chem. Commun. 2006, 3540-3542.
   PubMed Web of Science ®Google Scholar
• Schiemenz, G. P. Z. Naturforsch. 2006, 61b, 535-554.
   Google Scholar
• Lack of space precludes to outline the individual formulae. Readers are referred to the original papers and to CSD.
   Google Scholar
• (a) Schiemenz, G. P.; Schiemenz, B.; Petersen, S.; Wolff, C. Chirality 1998, 10, 180-189;
   Web of Science ®Google Scholar
  (b) Schiemenz, G. P. Chem. Listy 1998, 92, 269-270;
   Google Scholar
  (c) Schiemenz, G. P. Phosphorus Sulfur Silicon 2000, 163, 185-202;
   Web of Science ®Google Scholar
  (d) Schiemenz, G. P.; Bukowski, R.; Eckholtz, L.; Varnskühler, B. Z. Naturforsch. 2000, 55b, 12-20;
   Google Scholar
  (e) Schiemenz, G. P.; Pörksen, S.; Näther, C. Z. Naturforsch. 2000, 55b, 841-854; Dyker, G.; Hagel, M.; Henkel, G.; Köckerlimg, M.; Näther, C.; Petersen, S.; Schiemenz, G. P. Z. Naturforsch. 2001, 56b, 1109-1116; Schiemenz, G. P.; Pörksen, S.; Dominiak, P. M.; Wozniak, K. Z. Naturforsch. 2002, 57b, 8-18;
   Google Scholar
  (h) Schiemenz, G. P.; Näther, C. Z. Naturforsch. 2002, 57b, 309-318;
   Google Scholar
  (i) Schiemenz, G. P. Z. Anorg. Allg. Chem. 2002, 628, 2597-2604;
   Web of Science ®Google Scholar
  (j) Dominiak, P. M.; Petersen, S.; Schiemenz, B.; Schiemenz, G. P.; Wozniak, K. J. Mol. Struct. 2005, 751, 172-183.
   Web of Science ®Google Scholar
• Slagt, M. Q.; Dijkstra, H. P.; McDonald, A.; Klein Gebbink, R. J. M.; Lutz, M.; Ellis, D. D.; Mills, A. M.; Spek, A. L.; van Koten, G. Organometallics 2003, 22, 27-29. Unfortunately, no reliable values of r(vdW)[Pd/Pt] are available; cf. Schiemenz, G. P. Z. Naturforsch. 2007, 62b, 235-243.
   Web of Science ®Google Scholar
• Mealli, C.; Pichierri, F.; Randaccio, L.; Zangrando, E.; Krumm, M.; Holtenrich, D.; Lippert, B. Inorg. Chem. 1995, 34, 3418-3424.
   Web of Science ®Google Scholar
• Schiemenz, G. P.; Petersen, S.; Pörksen, S. Z. Naturforsch. 2003, 58b, 715-724, note [12].
   Google Scholar
• Wehman-Ooyevaar, I. C. M.; Grove, D. M.; van der Sluis, P.; Spek, A. L.; van Koten, G. J. Chem. Soc., Chem. Commun. 1990, 1367-1369; Wehman-Ooyevaar, I. C. M.; Grove, D. M.; Kooijman, H.; van der Sluis, P.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 9916-9924.
   Google Scholar
• Day, R. O.; Prakasha, T. K.; Holmes, R. R.; Eckert, H. Organometallics 1994, 13, 1285-1293; Prakasha, T. K.; Srinivasan, S.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. J. Am. Chem. Soc. 1995, 117, 10003-10009. Cf. Schiemenz et al.23, 25d,e,g,i,j
   Web of Science ®Google Scholar
• Faller, J. W.; Sarantopoulos, N. Organometallics 2004, 23, 2008-2014.
   Web of Science ®Google Scholar
• cf. d(Pd ←N) = 203.4 pm in [Pd(2,2′-bipyridyl)2]2+: Chieh, P. C. J. Chem. Soc., Dalton Trans. 1972, 1643-1646.
   Google Scholar
• Wilkinson, G.; Gillard, R. D.; McCleverty, J. A. (Eds.), Comprehensive Coordination Chemistry Vol. 5, Pergamon Press: Oxford, 1987.
   Google Scholar
• Roundhill, D. M. Platinum, in: Wilkinson et al.,33 351–531, p. 422.
   Google Scholar
• Barnard, C. F. J.; Russell, M. J. H. Palladium, in: Wilkinson et al.,33 1099–1130, p. 1115. Cf. Leyssens, T.; Peeters, D.; Orpen, A. G.; Harvey, J. N. Organometallics 2007, 26, 2637-2645.
   Google Scholar
• Haaland, A. Angew. Chem. 1989, 101, 1017-1032, Angew. Chem., Int. Ed. Engl. 1989, 28, 992.
   Google Scholar
• Sibert, J. W.; Forshee, P. B.; Lynch, V. Inorg. Chem. 2005, 44, 8602-8609.
   PubMed Web of Science ®Google Scholar
• Yamasaki, T.; Ozaki, N.; Saika, Y.; Ohta, K.; Goboh, K.; Nakamura, F.; Hashimoto, M.; Okeya, S. Chem. Lett. 2004, 33, 928-929.
   Web of Science ®Google Scholar
• Phillips, I. G.; Steel, P. J. J. Organomet. Chem. 1991, 410, 247-255.
   Web of Science ®Google Scholar
• Maassarani, F.; Pfeffer, M.; Spek, A. L.; Schreurs, A. M. M.; van Koten, G. J. Am. Chem. Soc. 1986, 108, 4222-4224.
   Web of Science ®Google Scholar
• Slawin, A. M. Z.; Smith, M. B.; Woollins, J. D. Polyhedron 1998, 17, 4465-4473.
   Web of Science ®Google Scholar
• Bardwell, D. A.; Crossley, J. G.; Jeffery, J. C.; Orpen, A. G.; Psillakis, E.; Tilley, E. E. M.; Ward, M. D. Polyhedron 1994, 13, 2291-2300.
   Web of Science ®Google Scholar
• Janssen, M. D.; Grove, D. M.; van Koten, G.; Spek, A. L. Rec. Trav. Chim. Pays-Bas 1996, 115, 286-292.
   Google Scholar
• Smith, M. B.; Slawin, A. M. Z. Inorg. Chim. Acta 2000, 299, 172-179.
   Web of Science ®Google Scholar
• Jones, N. D.; Foo, S. J. L.; Patrick, B. O.; James, B. R. Inorg. Chem. 2004, 43, 4056-4063.
   PubMed Web of Science ®Google Scholar
• Yamashita, M.; Kamura, K.; Yamamoto, Y.; Akiba, K.-y. Chem. Eur. J. 2002, 8, 2976-2979.
   PubMed Web of Science ®Google Scholar
• Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardia, M.; Bonjoch, J. Organometallics 2004, 23, 1438-1447.
   Web of Science ®Google Scholar
• Coles, S. J.; Durran, S. E.; Hursthouse, M. B.; Slawin, A. M. Z.; Smith, M. B. New J. Chem. 2001, 25, 416-422.
   Web of Science ®Google Scholar
• Foo, S. J. L.; Jones, N. D.; Patrick, B. O.; James, B. R. Chem. Commun. 2003, 988-989.
   PubMed Web of Science ®Google Scholar
• Clemente, D. A.; Marzotto, A. Acta Crystallogr. B 2003, 59, 43-50.
   PubMed Web of Science ®Google Scholar
• Jones, N. D.; Meessen, P.; Losehand, U.; Patrick, B. O.; James, B. R. Inorg. Chem. 2005, 44, 3290-3298.
   PubMed Web of Science ®Google Scholar
• Wang, Y.; Li, X.; Sun, J.; Ding, K. Organometallics 2003, 22, 1856-1862.
   Web of Science ®Google Scholar
• Viciu, M. S.; Kelly, III, R. A.; Stevens, E. D.; Naud, F.; Studer, M.; Nolan, S. P. Org. Lett. 2003, 5, 1479-1482.
   PubMed Web of Science ®Google Scholar
• Maassarani, F.; Pfeffer, M.; Le Borgne, G.; Jastrzebski, J. T. B. H.; van Koten, G. Organometallics 1987, 6, 1111-1118.
   Web of Science ®Google Scholar
• Crociani, L.; Bandoli, G.; Dolmella, A.; Basato, M.; Corain, B. Eur. J. Inorg. Chem. 1998, 1811-1820.
   Web of Science ®Google Scholar
• Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937-1948.
   Web of Science ®Google Scholar
• Pfeiffer, J.; Kickelbick, G.; Schubert, U. Organometallics 2000, 19, 957-959.
   Web of Science ®Google Scholar
• Cooper, M. K.; Hair, N. J.; Yaniuk, D. W. J. Organomet. Chem. 1978, 150, 157-170.
   Web of Science ®Google Scholar
• Wehman, E.; van Koten, G.; Hardeman, G.; Stam, C. H.; Pfeffer, M. Rec. Trav. Chim. Pays-Bas 1988, 107, 536-542.
   Google Scholar
• Spek, A. L.; submitted to CSD, CCDC 114063.
   Google Scholar
• Pfeiffer, J.; Kickelbick, G.; Schubert, U. Organometallics 2000, 19, 62-71.
   Web of Science ®Google Scholar
• Cooper, M. K.; Yaniuk, D. W.; McPartlin, M. J. Organomet. Chem. 1979, 166, 241-249.
   Web of Science ®Google Scholar
• van Beek, J. A. M.; van Koten, G.; Wehman-Ooyevaar, I. C. M.; Smeets, W. J. J.; van der Sluis, P.; Spek, A. L. J. Chem. Soc., Dalton Trans. 1991, 883-893.
   Google Scholar
• Smeets, W. J. J.; Spek, A. L.; van Beek, J. A. M.; van Koten, G. Acta Crystallogr. C 1992, 48, 745-747.
   Web of Science ®Google Scholar
• Smeets, W. J. J.; Spek, A. L.; van Beek, J. A. M.; van Koten, G. Acta Crystallogr. C 1992, 48, 1303-1305.
   Web of Science ®Google Scholar