Conformational preferences of sterically congested 2-imidazolidinone using X-ray analysis and computational studies. Part 1: Trans-1-acetyl-4,5-di-tert-butyl-2-imidazolidinone

Journal of Molecular Structure

Volumn 969, Issue 1-3, 2010, Pages 145-154

  Abdel Aziz, Alaa A M ^a   Al Omar, Mohamed A ^a   El Azab, Adel S ^a   Kunieda, Takehisa ^b  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b SOJO UNIVERSITY   (Japan)

Author keywords

2 Imidazolidinone; Conformational analysis; X ray crystal structure

Indexed keywords

COMPUTATIONAL STUDIES; CONFORMATIONAL ANALYSIS; CONFORMATIONAL PREFERENCES; INTERMOLECULAR HYDROGEN BONDING; SEMI-EMPIRICAL; STERICALLY CONGESTED; X RAY CRYSTAL STRUCTURES;

CONFORMATIONS; HYDROGEN BONDS; X RAY ANALYSIS;

CRYSTAL STRUCTURE;

EID: 77949490471     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2010.01.061     Document Type: Article

References (73)

1. Meyers A.I., Seefeld M.A., Lefker B.A., Blake J.F., and Williard P.G. J. Am. Chem. Soc. 120 (1998) 7429
2. Roos G.H.P.S. Afr. J. Chem. 51 (1998) 7
3. Hashimoto N., Ishizuka T., and Kunieda T. Tetrahedron Lett. 35 (1994) 721
4. Abdel-Aziz A.A.-M., Okuno J., Tanaka S., Ishizuka T., Matsunagae H., and Kunieda T. Tetrahedron Lett. 41 (2000) 8533
5. R.L. Hudkins, A.L. Zulli, D.R. Reddy, D.E. Gingrich, M. Tao, N.C. Becknell, J.L. Diebold, T.L. Underiner, US Patent 2005143442, 2005.
6. Goodacfre C.J., Bromidge L.P., Clapham D., King F.D., Lovell P.J., Allen M., Campbell L.P., Holland V., Riley G.J., Starr K.R., Trail B.K., and Wood M.D. Biorg. Med. Chem. Lett. 15 (2005) 4989
7. L. Gong, R.S. Wilhelm, US Patent 2005090504, 2005.
8. H. Ochiai, Y. Watanabe, Y. Murotani, H. Fukuda, O. Yoshino, S. Minami, T. Hayashi, K. Momonoi, GB 2233330, 1991.
9. Araújo M.A., Born J., Capela R., Casimiro C., Chambel P., Gomes P., Iley J., Lopes F., Morais J., Moreira R., Oliveira E., Rosário V., and Vale N. J. Med. Chem. 48 (2005) 888
10. Choo H.-Y.P., Choi S., Jung S.-H., Koh H.Y., and Pae A.N. Bioorg. Med. Chem. 11 (2003) 4585
11. Theophanides T., and Harvey P.D. Coord. Chem. Rev. 76 (1987) 237
12. Brandts J.F., and Hunt L. J. Am. Chem. Soc. 89 (1967) 4826
13. Nozaki Y., and Tanford C. J. Biol. Chem. 238 (1963) 4074
14. Myers J.K., Pace C.N., and Scholtz J.M. Protein Sci. 4 (1995) 2138
15. Keuleers R., Desseyn H.O., Rousseau B., and Van Alsenoy C. J. Phys. Chem. A 103 (1999) 4621
16. Worsham J.E., Levy H.A., and Peterson S.W. Acta Cryst. 10 (1957) 319
17. Waldron R.D., and Badger R.M. J. Chem. Phys. 18 (1950) 566
18. Swaminathan S., Craven B.M., and McMullan R.K. Acta Cryst. B 40 (1984) 300
19. Rousseau B., Van Alsenoy C., Keuleers R., and Desseyn H.O. J. Phys. Chem. A 102 (1998) 6540
20. Rousseau B., Keuleers R., Desseyn H.O., Geise H.J., and Van Alsenoy C. Chem. Phys. Lett. 302 (1999) 55
21. Gobbi A., and Frenking G. J. Am. Chem. Soc. 115 (1993) 2362
22. Dixon D.A., and Matzuzawa N. J. Phys. Chem. 98 (1994) 3967
23. Ha T.-K., and Puebla C. Chem. Phys. 181 (1994) 47
24. Godfrey P.D., Brown R.D., and Hunter A.N. J. Mol. Struct. 413 (1997) 405
25. Brown R.D., Godfrey P.D., and Storey J. J. Mol. Spectrosc. 58 (1975) 445
26. Gora R.W., Bartkowiak W., Roszak S., and Leszczynski J. J. Chem. Phys. 117 (2002) 1031
27. Dugave C., and Demange L. Chem. Rev. 103 (2003) 2475
28. Steward W.E., and Siddall III T.H. Chem. Rev. 70 (1970) 517
29. W.J. Hehre, Dealing with Conformationally Flexible Molecules, Practical Strategies for Electronic Structure Calculations, Wavefunction, 1995 (Chapter 6).
30. Abdel-Aziz A.A.-M., Matsunaga H., and Kunieda T. Tetrahedron Lett. 42 (2001) 6565
31. SIR92:. Altomare A., Burla M.C., Camalli M., Cascarano M., Giacovazzo C., Guagliardi A., and Polidori G. J. Appl. Cryst. 27 (1994) 435
32. DIRDIF 94: P.T. Beurskens, G. Admiraal, G. Beurskens, W.P. Bosman, R. de Gelder, R. Israel, J.M.M. Smits, The DIRDIF-94 Program System, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1994.
33. 2 (Fo) = e . s . d . based on counting; p = p -factor.)
34. 2 / (No - Nv)); where : No = number of observations; Nv = number of variables.)
35. D.T. Cromer, J.T. Waber, International Tables for X-ray Crystallography, vol. IV, The Kynoch Press, Birmingham, England, 1974 (Table 2.2 A).
36. Ibers J.A., and Hamilton W.C. Acta Cryst. 17 (1964) 781
37. Creagh D.C., and McAuley W.J. In: Wilson A.J.C. (Ed). International Tables for Crystallography vol. C (1992), Kluwer Academic Publishers, Boston 219-222 (Table 4.2.6.8)
38. Creagh D.C., and Hubbell J.H. In: Wilson A.J.C. (Ed). International Tables for Crystallography vol. C (1992), Kluwer Academic Publishers, Boston 200-206 (Table 4.2.4.3)
39. teXsan: Crystal Structure Analysis Package, Molecular Structure Corporation, 1985 and 1992.
40. HyperChem: Molecular Modeling System, Hypercube, Inc., Release 8.0.6, Florida, USA, 1995-2009.
41. Profeta S., and Allinger N.L. J. Am. Chem. Soc. 107 (1985) 1907
42. Abdel-Aziz A.A.-M. Eur. J. Med. Chem. 42 (2007) 614
43. Rocha G.B., Freire R.O., Simas A.M., and Stewart J.J.P. J. Comput. Chem. 27 (2006) 1101
44. Parr R.G., and Yang W. Density-Functional Theory of Atoms and Molecules (1999), Oxford University Press, New York
45. Koch W., and Holthausen M.C. A Chemist's Guide to Density Functional Theory. second ed. (2001), Wiley, Weinheim
46. Lee C., Yang C.W., and Parr R.W. Phys. Rev. B 37 (1998) 785
47. Becke A.D. J. Chem. Phys. 98 (1993) 1372
48. Becke A.D. Phys. Rev. A 38 (1998) 3098
49. Hariharan P.C., and Pople J.A. Theor. Chim. Acta 28 (1973) 213
50. Wolinski K., and Sadlej A.J. Mol. Phys. 41 (1980) 1419
51. Wolinski K., Hinton J.F., and Pulay P. J. Am. Chem. Soc. 112 (1990) 8251
52. Steed J.W. Cryst. Engng Commun. 5 (2003) 169
53. Flippen J.L. Acta Cryst. B29 (1973) 1756
54. Ueda H., Onishi H., and Nagai T. Acta Cryst. C42 (1986) 462
55. Kapon M., and Reisner G.M. Acta Cryst. C45 (1989) 780
56. Peeters O.M., Blaton N.M., and De Ranter C.J. Acta Cryst. C40 (1984) 1748
57. Park K.-L., Moon B.-G., Jung S.-H., Kim J.-G., and Suh I.-H. Acta Cryst. C56 (2000) 1247
58. Allen F.H., Kennard O., Watson D.G., Brammer L., Orpen A.G., and Taylor R. J. Chem. Soc. Perkin Trans. II (1987) S1-S19
59. Caron A. Acta Cryst. B25 (1969) 404
60. Vaughan P., and Donohue J. Acta Cryst. 5 (1952) 530
61. Caron A., and Donohue J. Acta Cryst. 17 (1964) 544
62. Grabowski S.J. Tetrahedron 54 (1998) 10153
63. S. Scheiner, Theoretical and Computational Chemistry, vol. 6, 1999, pp. 571-591.
64. Mitchell J.B.O., and Price S.L. Chem. Phys. Lett. 154 (1989) 267
65. Gung B.W., and Zhu Z. Tetrahedron Lett. 37 (1996) 2189
66. Taylor R., Kennard O., and Versichel W. J. Am. Chem. Soc. 106 (1984) 244
67. Taylor R., Kennard O., and Versichel W. J. Am. Chem. Soc. 105 (1983) 5761
68. Desiraju G.R., Sarma J.A.R.P., and Krishna T.S.R. Chem. Phys. Lett. 131 (1986) 124
69. Burley J.C., Gilmour R., Prior T.J., and Day G.M. Acta Cryst. C64 (2008) o10
70. Santos A.G., Candeias S.X., Afonso C.A.M., Jenkins K., Caddick S., Treweeke N.R., and Pardoe D. Tetrahedron 57 (2001) 6607
71. Vaschetto M.E., Retamal B.A., and Monkman A.P. J. Mol. Struct. (Theochem) 468 (1999) 209
72. Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J. J. Am. Chem. Soc. 107 (1985) 3902
73. Stewart J.J.P. J. Comput. Chem. 10 (1989) 209