Quantum mechanical calculations of conformationally relevant 1H and 13C NMR chemical shifts of calixarene systems

Organic Letters

Volumn 7, Issue 26, 2005, Pages 5757-5760

  Bifulco, Giuseppe ^a   Gomez Paloma, Luigi ^a   Riccio, Raffaele ^a   Gaeta, Carmine ^a   Troisi, Francesco ^a   Neri, Placido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 30144438056     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052166g     Document Type: Article

References (35)

1. For general reviews on calixarenes, see: (a) Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, UK, 1998.
2. (b) Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens J., Eds.; Kluwer: Dordrecht, The Netherlands, 2001.
3. Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, UK, 1989; pp. 110-111.
4. Kanamathareddy, S.; Gutsche, C. D. J. Org. Chem. 1992, 57, 3160.
5. (a) Jaime, C.; de Mendoza, J.; Prados, P.; Nieto, P. M.; Sanchez, C. J. Org. Chem. 1991, 56, 3372.
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9. 1H Δδ value of 1.55 (Martino, M.; Gaeta, C.; Neri, P. Tetrahedron Lett. 2004, 45, 3387).
10. 1H Δδ5 value up to 1.86 (Arduini, A.; Pochini, A.; Secchi, A. Eur. J. Org. Chem. 2000, 2325).
11. Barone, G.; Gomez-Paloma, L.; Duca, D.; Silvestri, A.; Riccio, R.; Bifulco, G. Chem. Eur. J. 2002, 8, 3233.
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25. See the Supporting Information for additional details.
26. Gutsche, C. D.; Dhawan, B.; No, K. H.; Muthukrishnan, R. J. Am. Chem. Soc. 1981, 103, 3782.
27. 1H NMR assignments (Groenen, L. C.; van Loon, J.-D.; Verboom, W.; Harkema, S.; Casnati, A.; Ungaro, R.; Pochini, A.; Ugozzoli, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1991, 113, 2385). See the Supporting Information for further details.
28. Gutsche, C. D.; Nam, K. C. J. Am. Chem. Soc. 1988, 110, 6153.
29. Gutsche, C. D.; Levine, J. A. J. Am. Chem. Soc. 1982, 104, 2652.
30. 1H NMR singlets for ArCH2Ar groups. See, for example: Appiah, W. O.; DeGreeff, A. D.; Razidlo, G. L.; Spessard, S. J.; Pink, M.; Young, V. G., Jr.; Hofmeister, G. E. Inorg. Chem. 2002, 41, 3656.
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33. Lipkowitz, K. B.; Pearl, G. J. Org. Chem. 1993, 58, 6729.
34. 2ν, conformation has to be attributed to the vertical and parallel orientation of a couple of distal rings. See, for comparison: Orda-Zgadzaj, M.; Wendel, V.; Fehlinger, M.; Ziemer, B.; Abraham, W. Eur. J. Org. Chem. 2001, 1549 (for additional details, see the Supporting Information).
35. This downfield shift induced by the oxygen atoms has also been experimentally proven for exo-calix[4]arenes (Biali, S. E.; Böhmer, V.; Brenn, J.; Frings, M.; Thondorf, I.; Vogt, W.; Wöhnert, J. J. Org. Chem. 1997, 62, 8350).