Thermally induced reversible conformational changes in the host-guest adduct of meso-tetramethyltetrakis(ethyl)calix[4]pyrrole

Tetrahedron Letters

Volumn 48, Issue 31, 2007, Pages 5481-5485

  Dey, Soumen ^a   Pal, Kuntal ^a   Sarkar, Sabyasachi ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

DTA; meso Tetramethyltetrakis(ethyl)calix 4 pyrrole; Powder XRD; TGA; X ray structure

Indexed keywords

PYRROLE DERIVATIVE; TETRAMETHYLTETRAKIS(ETHYL)CALIX[4]PYRROLE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; HYDROGEN BOND; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; THERMODYNAMICS; THERMOGRAVIMETRY; X RAY CRYSTALLOGRAPHY; X RAY POWDER DIFFRACTION;

EID: 34347337512     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.168     Document Type: Article

References (37)

1. Gale P.A., Sessler J.L., and Kral V. Chem. Commun. (1998) 1-8
2. Sessler J.L., Gross D.E., Cho W., Lynch V.M., Schmidtchen F.P., Bates G.W., Light M.E., and Gale P.A. J. Am. Chem. Soc. 128 (2006) 12281-12288
3. Golder A.J., Milgrom L.R., Nolan K.B., and Povey D.C. J. Chem. Soc., Chem. Commun. (1989) 1751-1752
4. Lee C.H., Na H.K., Yoon D.W., Won D., Cho W., Lynch V.M., Shevchuk S.V., and Sessler J.L. J. Am. Chem. Soc. 125 (2003) 7301-7306
5. Woods C.J., Camiolo S., Light M.E., Coles S.J., Hursthouse M.B., King M.A., Gale P.A., and Essex J.W. J. Am. Chem. Soc. 124 (2002) 8644-8652
6. Camiolo S., and Gale P.A. Chem. Commun. (2000) 1129-1130
7. Bhattacharya D., Dey S., Maji S., Pal K., and Sarkar S. Inorg. Chem. 44 (2005) 7699-7701
8. Floriani C. Chem. Commun. (1996) 1257-1263 and references cited therein
9. Bachmann J., and Nocera D.G. J. Am. Chem. Soc. 127 (2005) 4730-4743
10. Bachmann J., and Nocera D.G. J. Am. Chem. Soc. 126 (2004) 2829-2837
11. Bachmann J., Hodgkiss J.M., Young E.R., and Nocera D.G. Inorg. Chem. 46 (2007) 607-609
12. Camiolo S., Coles S.J., Gale P.A., Hursthouse M.B., and Sessler J.L. Acta Crystallogr., Sect. E 57 (2001) 816-817
13. Anzenbacher P., Jursikova K., Lynch V.M., Gale P.A., and Sessler J.L. J. Am. Chem. Soc. 121 (1999) 11020-11021
14. Camiolo S., Coles S.J., Gale P.A., Hursthouse M.B., and Paver M.A. Acta Crystallogr., Sect. E 57 (2001) 258-260
15. Inoue H.K., Inoue T., and Ono N. Org. Biomol. Chem. 1 (2003) 3857-3865
16. Lynch V.M., Gale P.A., Sessler J.L., and Madeiros D. Acta Crystallogr., Sect. C 57 (2001) 1426-1427
17. Anzenbacher P., Jursikova K., Shriver J.A., Miyaji H., Lynch V.M., Sessler J.L., and Gale P.A. J. Org. Chem. 65 (2000) 7641-7645
18. Su X., Zhou Z., Zhu S., Lin H., Leng X., Weng L., and Chen Y. J. Chem. Res. (2000) 538-539
19. Lehmann C., Schweizer B., Leumann C., and Eschenmoser A. Helv. Chim. Acta 80 (1997) 1421-1442
20. Jacoby D., Floriani C., Chiesi-Villa A., and Rizzoli C. J. Chem. Soc., Chem. Commun. (1991) 790-791
21. Anzenbacher P., Try A.C., Miyaji H., Jursikova K., Lynch V.M., Marquez M., and Sessler J.L. J. Am. Chem. Soc. 122 (2000) 10268-10272
22. Nielsen K.A., Cho W.S., Jeppesen J.O., Lynch V.M., Becher J., and Sessler J.L. J. Am. Chem. Soc. 126 (2004) 16296-16297
23. Gale P.A., Sessler J.L., Kral V., and Lynch V. J. Am. Chem. Soc. 118 (1996) 5140-5141
24. Allen W.E., Gale P.A., Brown C.T., Lynch V.M., and Sessler J.L. J. Am. Chem. Soc. 118 (1996) 12471-12472
25. Anzenbacher P., Nishiyabu R., and Palacios M.A. Coord. Chem. Rev. 250 (2006) 2929-2938
26. Baeyer A. Ber. Dtsch. Chem. Ges. 19 (1886) 2184-2185
27. Dey S., Pal K., and Sarkar S. Tetrahedron Lett. 47 (2006) 5851-5854 and Refs. 12-30 cited therein
28. Miyazu H., Anzenbacher Jr. P., Sessler J.L., Bleasdale E.R., and Gale P.A. Chem. Commun. (1999) 1723-1724
29. Gale P.A., Twyman L.J., Handlin C.I., and Sessler J.L. Chem. Commun. (1999) 1851-1852
30. Gale P.A., Hursthouse M.B., Light M.E., Sessler J.L., Warriner C.N., and Zimmerman R.S. Tetrahedron Lett. 42 (2001) 6759-6762
31. Wu Y., Wang D., and Sessler J.L. J. Org. Chem. 66 (2001) 3739-3746
32. Daniel de. Namor A., and Shehab M. J. Phys. Chem. 107 (2003) 6462-6468
33. 7 1·2EtOH and 1·2MeOH were crystallized by slow diffusion of water into ethanol or methanol solutions of 1 upon standing for 2 days at 4 °C under aerobic conditions. 1·2DMF was crystallized by slow diffusion of water into a DMF solution containing 1 at 4 °C for 3 days under aerobic conditions. 1 was found to be fairly soluble in paraffin oil, hence single crystals for X-ray diffraction were mounted for data collection only after coating with heavier Paratone-N.
34. 3, methyl, J = 5.84 Hz). TGA/DTA: Mass loss was found to start at ∼120 °C and was found to be 23% as per calculated. From DTA, two endothermic peaks were found to occur at around 128 °C and 155 °C for mass loss and melting of the compound, respectively. Here also decomposition occurred around 250 °C.
35. -1.
36. -1. Crystallographic data for 1·2EtOH and 1·2DMF have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 635032 and 635033. Copies of the data can be obtained free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk.
37. 3.