Synthesis, structural and conformational study of chromane derivatives

Journal of Molecular Structure

Volumn 937, Issue 1-3, 2009, Pages 139-145

  Ciolkowski, Michal ^a   Malecka, Magdalena ^b   Modranka, Roman ^a   Budzisz, Elzbieta ^a  

^a MEDICAL UNIVERSITY OF LODZ   (Poland)

^b UNIVERSITY OF LODZ   (Poland)

Author keywords

1H NMR study; Chromane derivatives; DFT calculation; Synthesis; X ray structure

Indexed keywords

ATOMS; CARBOXYLIC ACIDS; COMPLEXATION; CONFORMATIONS; ESTERIFICATION; ESTERS; HYDROGEN; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; PROBABILITY DENSITY FUNCTION;

1H NMR STUDY; CHROMANE DERIVATIVES; DFT CALCULATION; SYNTHESIS; X-RAY STRUCTURE;

X RAY ANALYSIS;

EID: 84962343508     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2009.08.028     Document Type: Article

References (42)

1. Budzisz E., Brzezinska E., Krajewska U., and Rozalski M. Eur. J. Med. Chem. 38 (2003) 597
2. Kostka K., and Zyner E. Chem. Anal. (Warsaw) 25 (1980) 61
3. Budzisz E., and Pastuszko S. Tetrahedron 55 (1999) 4815
4. Budzisz E., Zieba R., Graczyk-Wojciechowska J., and Nawrot B. New J. Chem. 26 (2002) 1799
5. Budzisz E., Malecka M., Lorenz I.-P., Mayer P., Kwiecień R., Paneth P., Krajewska U., and Rozalski M. Inorg. Chem. 45 24 (2006) 9688
6. Rosenau T., Potthast A., Ebner G., Hofinger A., and Kosma P. Org. Lett. 4 (2002) 1257
7. Budzisz E. Farmacja Polska 59 (2003) 677
8. Harbone J.B., and Williams C.A. Phytochemistry 55 (2000) 481
9. Liebler D.C., Burr J.A., Matsumoto S., and Matsuo M. Chem. Res. Toxicol. 6 (1993) 351
10. Karplus M. J. Chem. Phys. 30 (1959) 11
11. J.T. Wrobel, Preparatyka i elementy syntezy organicznej, PWN, Warsaw, 1983, pp. 9-52.
12. Coppola G.M., and Dodsworth R.W. Synthesis 7 (1981) 523
13. Stoe and Cie, Software for IPDS-II, Darmstadt, Germany, 2000.
14. G.M. Sheldrick, Program for the Refinement of Crystal Structures SHELXS-97, University of Göttingen, Germany, 1997.
15. G.M. Sheldrick, Program for the Refinement of Crystal Structures SHELXL-97, University of Göttingen, Germany, 1997.
16. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision D.01, Gaussian Inc., Wallingford, CT, 2004.
17. Stephens P.J., Devlin F.J., Chabalowski C.F., and Frisch M.J. J. Phys. Chem. 98 (1994) 11623
18. Miertus S., Scrocco E., and Tomasi J. J. Chem. Phys. 55 (1981) 117
19. Cances E., Mennucci B., and Tomasi J. J. Chem. Phys. 107 (1997) 3032
20. Cossi M., Barone V., Mennucci B., and Tomasi J. Chem. Phys. Lett. 286 (1998) 253
21. Tomasi J., Mennucci B., and Cances E. J. Mol. Struct. (THEOCHEM) 464 (1999) 211
22. Ditchfield R. Mol. Phys. 27 (1974) 789
23. Wolinski K., Hinton J.F., and Pulay P. JACS 112 (1990) 8251
24. Sychrovsky V., Grafenstein J., and Cremer D. J. Chem. Phys. 113 (2000) 3530
25. Helgaker T., Watson M., and Handy N.C. J. Chem. Phys. 113 (2000) 9402
26. Contreras R.H., Barone V., Facelliand J.C., and Peralta J.E. Ann. Rep. NMR S. 51 (2003) 167
27. Macrae C.F., Edgington P.R., McCabe P., Pidcock E., Shields G.P., Taylor R., Towler M., and van de Streek J. J. Appl. Crystallogr. 39 (2006) 453
28. Macrae C.F., Bruno I.J., Chisholm J.A., Edgington P.R., McCabe P., Pidcock E., Rodriguez-Monge L., Taylor R., van de Streek J., and Wood P.A. J. Appl. Crystallogr. 41 (2008) 466
29. Payard M., and Couquelet J. Synthesis (1979) 889
30. Hanaya K., Koga Y., Yamagugchi A., Kudo H., and Chow Y.L. Nouveau J. Chem. 6 (1982) 149
31. Drewes S.E., and Roux D.G. Biochem. J. 90 (1964) 343
32. Yamaguchi S., Ito S., Nakamura A., and Inoue N. Bull. Chem. Soc. Jpn. 38 (1965) 2187
33. Hanaya K. Bull. Chem. Soc. Jpn. 43 (1970) 442
34. Yamaguchi S., Kabuto K., Ninomiya Y., and Inoue N. Bull. Chem. Soc. Jpn. 43 (1970) 3952
35. Kabuto K., Kikuchi Y., Yamaguchi S., and Inoue N. Bull. Chem. Soc. Jpn. 46 (1973) 1839
36. Magalhaes A.F., Ruiz A.L.T.G., Tozzi A.M.G.A., and Magalhaes E.G. Phytochemistry 52 (1999) 1681
37. Mateus N., Oliveira J., Santos-Buelga C., Silva A.M.S., and de Freitas V. Tetrahedron Lett. 45 (2004) 3455
38. Cremer D., and Pople J.A. J. Am. Chem. Soc. 97 (1975) 1354
39. Nardelli M. Acta Crystallogr. C 39 (1983) 1141
40. G.R. Desiraju, T. Steiner, The weak hydrogen bond in structural chemistry and biology, in: IUCr Monographs on Crystallography, vol. 9, Oxford University Press/International Union of Crystallography, Oxford, 1999.
41. Allen A.H., Kennard O., Watson D.G., Brammer L., Orpen A.G., and Taylor R. J. Chem. Soc. Perkin Trans. 2 (1987) S1
42. A.L. Spek, PLATON - Molecular Geometry Program, University of Utrecht, The Netherlands, 1998.