K. Al-Farhan et al. / Journal of Molecular Structure 994 (2011) 269–275
275
these phthalimide derivatives was noticed to be related to the
presence of a dione–acetyl group conjugation.
[25] P. Lidstrom, J. Tierney, B. Wathey, J. Westman, Tetrahedron 57 (2001) 9225.
[
[
[
26] L. Perreux, A. Loupy, Tetrahedron 57 (2001) 9199.
27] A. Loupy, C. R. Chim. 7 (2004) 103.
28] R.S. Varma, Tetrahedron 58 (2002) 1235.
Acknowledgements
[29] R.S. Varma, R. Dahiya, S. Kumar, Tetrahedron Lett. 38 (1997) 2039.
[
[
31] Rigaku, Crystal Clear, Crystal Structure Analysis Package, Rigaku, 9009 New
Trails Dr., The Woodlands, TX 77381, 2007.
(
The authors are indebted to the Scientific Research Center,
College of Science (Project No. Chem-2010/11) and to the Distin-
guished Scientist Fellowship Program (DSFP) at King Saud Univer-
sity, Riyadh, Saudi Arabia for supporting this work.
[
[
[
[
32] G.M. Sheldrick, Acta. Cryst. A 64 (2008) 112.
33] Diamond, Crystal Impact GbR ver 3.1e (2007) Bonn, Germany.
34] W.D.S. Motherwell, G.P. Shields, F.H. Allen, Acta Cryst. B 55 (1999) 1044.
35] SPARTAN, SPARTAN’08, Wavefunction, Ver. 1.2.0., 18401 Von Karman Avenue,
Suite Irvine, CA 92612, USA, 2009.
Appendix A. Supplementary material
[
[
36] A.D. Becke, Phys. Rev. A38 (1988) 3098.
37] J.D. Perdew, Phys. Rev. B33 (1986) 8822.
Contained in the supplementary data are a more detailed pre-
sentation of microwave and conventional synthetic procedures
and its yields comparison. CCDC 778829–778831 contains the sup-
ing.html or from Cambridge Crystallographic Data Centre (CCDC),
[38] P.C. Hariharan, J.A. Pople, Theor. Chim Acta 28 (1973) 213.
[
[
39] T.v. der Wijst, C.F. Guerra, M. Swart, F.M. Bickelhaupt, Chem. Phys. Lett. 426
2006) 415.
40] K.E. Riley, B.T.O. Holt, K.M. Merz Jr., J. Chem. Theory Comput. 3 (2) (2007) 407.
(
[41] A.D. Rabuck, G.E. Scuseria, Theor. Chim. Acta 104 (2000) 439.
[
42] J.E. Del Bene, Encyclopedia of Computational Chemistry, vol. 1, Wiley, Chester,
England, 1998. p. 1263.
[
43] L. Hirsfeld, Theor. Chim. Acta 44 (1977) 129.
1
2 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (0)1223 336033.
[44] S.K. Wolff, D.J. Grimwood, J.J. McKinnon, D. Jayatilaka, M.A. Spackman,
CrystalExplorer, Version 2.1, University of Western Australia, Australia,
2007.
[
[
45] E.W. Koneman, S.D. Allen, W.M. Janda, P.C. Screckenberger, W.C. Winn, Colour
Atlas and Textbook of Diagnostic Microbiology, Lippincott-raven Publishers,
Philadelphia, 1997.
46] A.K. Bose, M.S. Manhas, M. Ghosh, V.S. Raju, K. Tabei, Z. Urbanczyklipkowska,
Heterocycles 30 (1990) 741.
References
[
[
1] A. Dasettimo, G. Primofiore, P.L. Ferrarini, M. Ferretti, P.L. Barili, N. Tellini, P.
Bianchini, Eur. J. Med. Chem. 24 (1989) 263.
2] M.F. Brana, M. Cacho, A. Ramos, M.T. Dominguez, J.M. Pozuelo, C. Abradelo,
M.F. Rey-Stolle, M. Yuste, C. Carrasco, C. Bailly, Org. Biomol. Chem. 1 (2003)
[
[
47] T. Vidal, A. Petit, A. Loupy, R.N. Gedye, Tetrahedron 56 (2000) 5473.
48] A. Stadler, B.H. Yousefi, D. Dallinger, P. Walla, E. Van der Eycken, N. Kaval, C.O.
Kappe, Org. Process Res. Dev. 7 (2003) 707.
[
[
49] H.D. Flack, Acta Cryst. A 39 (1983) 876.
50] J. Bernstein, R.E. Davis, L. Shimoni, N.L. Chang, Angew. Chem. In. Ed. 34 (1995)
6
48.
[
[
[
[
[
3] M.F. Brana, A. Ramos, Curr. Med. Chem. 1 (2001) 237.
4] C.W. Schellhammer, J. Schroeder, Angew. Chem. Int. Ed. 14 (1975) 665.
5] W.W. Stewart, Nature 292 (1981) 17.
6] B. Ramachandram, A. Samanta, Chem. Commun. (1997) 1037.
7] T.C. Barros, S. Brochsztain, V.G. Toscano, P. Berci, M.J. Politi, J. Photochem.
Photobiol. A – Chem. 111 (1997) 97.
8] M.J. Ahrens, L.E. Sinks, B. Rybtchinski, W.H. Liu, B.A. Jones, J.M. Giaimo, A.V.
Gusev, A.J. Goshe, D.M. Tiede, M.R. Wasielewski, J. Am. Chem. Soc. 126 (2004)
1555.
[
[
[
51] G.R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and
Biology, Oxford University Press, Oxford, 1999.
52] F.A. Cotton, L.M. Daniels, G.T. Jordan, C.A. Murillo, Chem. Commun. (1997)
1673.
53] G.R. Desiraju, Encyclopedia of Supramolecular Chemistry, Marcel Dekker, New
York, 2004.
[
[
[
[
[
54] T. Steiner, Angew. Chem. In. Ed. 41 (2002) 48.
55] T. Steiner, G.R. Desiraju, Chem. Commun. (1998) 891.
56] J.J. Novoa, B. Tarron, M.H. Whangbo, J.M. Williams, J. Chem. Phys. 95 (1991)
8
284.
9] P. Yan, A. Chowdhury, M.W. Holman, D.M. Adams, J. Phys. Chem. B109 (2005)
24.
7
5179.
[
[
[
10] M.W. Holman, R.C. Liu, D.M. Adams, J. Am. Chem. Soc. 125 (2003) 12649.
11] N. Barooah, R.J. Sarma, J.B. Baruah, Cryst. Growth Des. 3 (2003) 639.
12] N. Kimizuka, T. Kawasaki, K. Hirata, T. Kunitake, J. Am. Chem. Soc. 117 (1995)
[
[
[
57] P. Seiler, L. Isaacs, F. Diederich, Helv. Chim. Acta 79 (1996) 1047.
58] T. van Mourik, F.B. van Duijneveldt, Theochem. – J. Mol. Struct. 341 (1995) 63.
59] X.J. Yan, S.M. Wang, M. Hodoscek, G.W.A. Milne, Theochem. – J. Mol. Struct.
6
360.
1
15 (1994) 279.
60] H. Bock, R. Dienelt, H. Schodel, Z. Havlas, J. Chem. Soc. – Chem. Commun.
1993) 1792.
61] A. Cappelli, G. Giorgi, M. Anzini, S. Vomero, S. Ristori, C. Rossi, A. Donati, Chem.
Eur. J. 10 (2004) 3177.
[
[
13] K. Kishikawa, S. Tsubokura, S. Kohmoto, M. Yamamoto, K. Yamaguchi, J. Org.
Chem. 64 (1999) 7568.
[
[
(
14] J.E.D. Davies, P. Finocchiaro, F.H. Herbstien, J.L. Atwood, J.E.D. Davies, D.D.
MacNicol, Inclusion Compounds, vol. 2, Academic press, New York, 1984.
15] A.A. Elasmy, M.A. Hafez, E.M. Saad, F.I. Taha, Trans. Met. Chem. 19 (1994) 603.
16] F. Jaber, F. Charbonnier, R. Faure, Acta Cryst. C 51 (1995) 1765.
17] G.K. Sandhu, S.S. Sandhu, Synth. React. Inorganic Met. – Org. Chem. 25 (1995)
–
[
[
[
[
[
[
62] G.R. Desiraju, J. Chem. Soc. – Chem. Commun. (1990) 454.
63] J.J. Novoa, F. Mota, Chem. Phys. Lett. 318 (2000) 345.
64] S. Tsuzuki, K. Honda, T. Uchimaru, M. Mikami, K. Tanabe, J. Am. Chem. Soc. 122
9
3.
(
2000) 11450.
[
18] S. Gomez-Ruiz, B. Gallego, M.R. Kaluderovic, H. Kommera, E. Hey-Hawkins, R.
Paschke, G.N. Kaluderovic, J. Organomet. Chem. 694 (2009) 2191.
19] L.H. Abdel-Rahman, Trans. Met. Chem. 26 (2001) 412.
20] E. Eliel, S.H. Willen, L.N. Mander, Stereochemistry of Organic Compounds,
Wiley, New York, 1994.
[
[
65] W.L. Zhu, X.J. Tan, C.M. Puah, J.D. Gu, H.L. Jiang, K.X. Chen, C.E. Felder, I. Silman,
J.L. Sussman, J. Phys. Chem. A104 (2000) 9573.
66] C.J. Cramer, Essentials of Computational Chemistry Theories and Models, 2nd
ed., Wiley, UK., 2004.
[
[
[
[
[
[
67] C.C. Møller, M.S. Plesset, Phys. Rev. (1934) 618.
[
21] E. Juaristi, Introduction to Stereochemistry and Conformational Analysis,
Wiley, New York, 1991.
68] J.J. McKinnon, D. Jayatilaka, M.A. Spackman, Chem. Commun. (2007) 3814.
69] J.J. McKinnon, M.A. Spackman, A.S. Mitchell, Acta Cryst. B 60 (2004) 627.
70] A.M. Pendas, V.L. Pueyo, E. Francisco, P.-M. Sanches, J. Chem. Phys. 3 (2002)
[
[
22] E. Juaristi, An. Quim. 93 (1997) 135.
23] A.H. Bedair, F.M. Ali, A.M. El-Agrody, F.A. Eid, M.A.A. El-Nassag, G. El-Sherbeny,
Acta Pharm. 56 (2006) 273.
1017.
[
71] E. Clementi, C. Roetti, At. Data Nucl. Data Tables 14 (1974) 177.
[
24] S. Caddick, Tetrahedron 51 (1995) 10403.