X-ray, 1H NMR and DFT study on 5-para-X-benzylidene-thiazolidine derivatives with X = Br, F

Journal of Molecular Structure: THEOCHEM

Volumn 851, Issue 1-3, 2008, Pages 63-74

  Chiş, Vasile ^a   Pîrnǎu, Adrian ^a   Vasilescu, Mihai ^a   Varga, Richard A ^a   Oniga, Ovidiu ^b  

^a BABE BOLYAI UNIVERSITY   (Romania)

^b IULIU HATIEGANU UNIVERSITY OF MEDICINE AND PHARMACY   (Romania)

Author keywords

DFT calculations; NMR; Tautomers; Thiazolidine 2 thione 4 one; X ray diffraction

Indexed keywords

EID: 84962426038     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2007.10.041     Document Type: Article

References (75)

1. Cohen M.L. Nature 406 (2000) 762
2. Shinabarger D.A. Exp. Opin. Invest. Drugs 8 (1999) 1195
3. Singh S.P., Parmar S.S., Raman K., and Sternberger V.I. Chem. Rev. 81 (1981) 175
4. Seneci P., Caspani M., Ripamonti F., and Ciabatti R. J. Chem. Soc. Perkin Trans. 1 16 (1994) 2345
5. Kavitha C.V., Basappa, Nanjunda Swamy S., Mantelingen K., Doreswamy S., Sridhar M.A., Shashidhara Prasad J., and Rangapa S. Bioorg. Med. Chem. 14 (2006) 2290
6. Billeter M. Perspect. Drug Discov. Des. 3 (1995) 151
7. Soto-Castro D., Evanghelista-Lara A., and Guadarrama P. Tetrahedron 16 (2006) 12116
8. Baias M., Pîrnǎu A., Chiş V., Cozar O., and Vasilescu M. J. Opt. Adv. Mat. 8 (2006) 205
9. Becke A.D. J. Chem. Phys. 98 (1993) 5648
10. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
11. Hehre W.J., Radom L., R Schleyer P.v., and Pople J.A. Ab Initio Molecular Orbital Theory (1986), Wiley, New York
12. Korth G., de Heer M.I., and Mulder P. J. Phys. Chem. A 106 (2002) 8779
13. Chiş V., Pîrnǎu A., Jurcǎ T., Vasilescu M., Simon S., Cozar O., and David L. Chem. Phys. 316 (2005) 153
14. Hsieh T.J., Lu L.H., and Su C.C. Biophys. Chem. 114 (2005) 13
15. Brycki B., Kowalczyk I., Werner J., Borowiak T., and Wolska I. J. Mol. Struct. 791 (2006) 137
16. Laihia K., Puszko A., Linnanto J., and Kolehmainen E. J. Mol. Struct. 783 (2006) 73
17. Dega-Szafran Z., Katrusiak A., and Szafran M. J. Mol. Struct. 785 (2006) 160
18. Krawczyk H., Pietras A., and Kraska A. Spectrochim. Acta A 66 (2007) 9
19. Dobrowolski J.Cz., Rode J.E., and Sadlej J. J. Mol. Struct. (Theochem.) 810 (2007) 129
20. Mirzarei M., Hadipour N.L., and Ahmadi K. Biophys. Chem. 125 (2007) 411
21. Schirmeister T., Breuning A., Murso A., Stalke D., Mladenovic M., Engels B., Szeghalmi A., Schmitt M., Kiefer W., and Popp J. J. Phys. Chem. A 108 (2004) 11398
22. Sheldrick G.M. SHELXTL-97, Program for Refinement of Crystal Structure (1997), University of Göttingen, Göttingen, Germany
23. DIAMOND - Visual Crystal Structure Information System, CRYSTAL IMPACT: Postfach 1251, D-53002 Bonn, Germany, 2001.
24. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M. W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh PA, 1998.
25. Zierkiewicz W., Michalska D., Czarnik-Matusewicz B., and Raspenk M. J. Phys. Chem. A 107 (2003) 4547
26. Peralta J.E., Scuseria G.E., Cheeseman J.R., and Frisch M.J. Chem. Phys. Lett. 375 (2003) 452
27. Tormena C.F., and da Silva G.V.J. Chem. Phys. Lett. 398 (2004) 466
28. Miertus S., Scrocco E., and Tomasi J. Chem. Phys. 55 (1981) 117
29. Cammi R., and Tomasi J. J. Comput. Chem. 16 (1995) 1449
30. Ditchfield R. Mol. Phys. 27 (1974) 789
31. Wolinski K., Hilton J.F., and Pulay P. J. Am. Chem. Soc. 112 (1990) 8251
32. Chruszcz K., Baranska M., Lewinski K., and Proniewicz L.M. Vib. Spectrosc. 32 (2003) 199
33. Chiş V. Chem. Phys. 300 (2004) 1
34. Sundaraganesan N., Ayyappan S., Umamahesvari H., and Dominic Joshua B. Spectrochim. Acta A 66 (2007) 17
35. Jensen S.J.K., Tang T.-H., and Csizmadia I.G. J. Phys. Chem. A 107 (2003) 8975
36. Sato T., Tsuneda T., and Hirao K. J. Chem. Phys. 123 (2005) 104307
37. Jeffrey G.A. An Introduction to Hydrogen Bonding (1997), Oxford University Press, New York
38. Steiner T. Angew. Chem. Int. Ed. 41 (2002) 48
39. Cygan R.T., Liang J.-J., and Kalinichev A.G. J. Phys. Chem. B 108 (2004) 1255
40. Tsiper E.V., and Burke K. J. Chem. Phys. 120 (2004) 1153
41. Cherkasov A. J. Chem. Inf. Comp. Sci. 43 (2003) 2039
42. Yang W., and Mortier W.J. J. Am. Chem. Soc. 108 (1986) 5708
43. Handschuh S., and Gasteiger J. J. Mol. Model. 6 (2000) 358
44. Winiwarter S., Ax F., Lennernäs H., Hallberg A., Pettersson C., and Karlén A. J. Mol. Graph. Model. 21 (2003) 273
45. Latosinska J.N. J. Mol. Graph. Model. 23 (2005) 329
46. Cao H., Zhang H., Zheng X., and Gao D. J. Mol. Graph. Model. 26 (2007) 236
47. Abraham R., Mobli M., and Smith R.J. Mag. Reson. Chem. 41 (2003) 26
48. Balaban A.T., Oniciu D.C., and Katritzky A.R. Chem. Rev. 104 (2004) 2777
49. Yan W., Xue Y., Zhu H., Zeng J., and Xie D. J. Comput. Chem. 25 (2004) 1833
50. Koparir M., Cetin A., and Cansiz A. Molecules 10 (2005) 475
51. Fu A., Li H., and Du D. J. Mol. Struct. (Theochem.) 767 (2006) 51
52. Henke K.R., Hutchinson A.R., Krepps M.K., Parkin S., and Atwood D.A. Inorg. Chem. 40 (2001) 4443
53. Wenska G., Taras-Goslinska K., Skalski B., Hug G.L., Carmichael I., and Marciniak B. J. Org. Chem. 70 (2005) 982
54. Roy G., and Mugesh G. J. Chem. Sci. 118 (2006) 619
55. Singh N.K., Butcher R.J., Triphati P., Srivastava A.K., and Bharty M.K. Acta Cryst. E 63 (2007) o782
56. Contreras J.G., and Madariaga S.T. J. Phys. Org. Chem. 16 (2003) 47
57. Sridharan V., Muthusubramanian S., Sivasubramanian S., and Polborn K. J. Mol. Struct. 707 (2004) 161
58. Breitmaier E. Structure Elucidation by NMR in Organic Chemistry (2002), John Wiley
59. Delaere D., Raspoet G., and Nguyen M.T. J. Phys. Chem. A 103 (1999) 171
60. Laurence C., El Ghomari M.J., LeQuestel J.-Y., Berthelot M., and Mokhlisse R. J. Chem. Soc. Perkin Trans. 2 (1998) 1545
61. Rodriguez C.F., Cunje A., Shoeib T., Chu I.K., Hopkinson A.C., and Siu K.W.M. J. Phys. Chem. A 104 (2000) 5023
62. Ferrer S., Naughton D.P., and Threadgill M.D. Tetrahedron 59 (2003) 3445
63. Hua H., Peng J., Fronczek F.R., Kelly M., and Hamann M.T. Bioorg. Med. Chem. 12 (2004) 6461
64. Nakata T., Yamada T., Taji S., Ohishi H., Wada S., Tokuda H., Sakuma K., and Tanaka R. Bioorg. Med. Chem. 15 (2007) 257
65. Gottlieb H.E., Kotlyar V., and Nudelman A. J. Org. Chem. 62 (1997) 7512
66. Friebolin H. Basic One and Two Dimensional NMR spectroscopy (2005), Wiley-VCH, Weinheim p. 60
67. Deng H., Lewandowicz A., Cahill S.M., Furneaux R.H., Tyler P.C., Girvin M.E., Callender R.H., and Schramm V.L. Biochemistry 43 (2004) 1980
68. Pazderski L., Lakomska I., Woitczak A., Szlyk E., Sitkovski J., Kozerski L., Kamienski B., Tousek J., and Marek R. J. Mol. Struct. 785 (2006) 205
69. Mayer I. J. Mol. Struct. (Theochem.) 255 (1992) 1
70. Thompson J.D., Xidos J.D., Sonbuchner T.M., Cramer C.J., and Truhlar D.G. Phys. Chem. Commun. 5 (2002) 117
71. Reed A.E., Weinstock R.B., and Weinhold F.J. J. Chem. Phys. 83 (1985) 735
72. Martin F., and Zipse H. J. Comput. Chem. 26 (2005) 97
73. Cramer C.J., and Truhlar D.G. J. Am. Chem. Soc. 115 (1993) 8810
74. Contreras J.G., and Alderete J.B. Chem. Phys. Lett. 232 (1995) 61
75. Yekeler H. J. Comput. Aided Mol. Des. 14 (2000) 243