Citation: AL-SEHEMI Abdullah G., Al-AMRI Reem S. Abdulaziz, IRFAN Ahmad. Characterization and Density Functional Theory Investigations of 3-Monoacylaminoquinazolinone Derivatives[J]. Acta Physico-Chimica Sinica, ;2013, 29(01): 55-63. doi: 10.3866/PKU.WHXB201210151 shu

Characterization and Density Functional Theory Investigations of 3-Monoacylaminoquinazolinone Derivatives

1.
1 Department of Chemistry, Faculty of Science, King Khalid University, Abha 61413, P.O. Box 9004, Saudi Arabia;
2 Unit of Science and Technology, Faculty of Science, King Khalid University, Abha 61413, P.O. Box 9004, Saudi Arabia

Received Date: 4 July 2012
Available Online: 15 October 2012
Fund Project: AL-AMRI ReemS. Abdulaziz was supported by the King Abdul Aziz City of Science and Technology (KACST) (GSP-18-138). (KACST) (GSP-18-138)

Several 3-aminoquinazolin-4-(3H)-one derivatives were synthesized and characterized. Using proton nuclear magnetic resonance (NMR) spectra, we have investigated the barriers to rotation around the N-N bond as a function of temperature. Changes in the NMR spectra at high temperatures are explained in terms of hindered rotations of the N-N bond. Free energies of activation for the rate determining stereochemical process were calculated to be as high as 67-75 kJ·mol^-1. Ground state molecular geometries and vibrational frequencies were calculated using the HF/6-31G^** and B3LYP/6-31G^** level of theories. The optimized bond lengths and bond angles are in od agreement with experimental values at both theoretical levels.
- 3-Monoacylaminoquinazolinones,
- Density functional theory,
- Geometry,
- NMR,
- IR
1. [1]
  
  (1) Panicker, C. Y.; Varghese, H. T.; Ambujakshan, K. R.; Mathew,S.; Ganguli, S.; Nanda, A. K.; Alsenoy, C. V. J. Raman Spectro.2009, 40, 1262. doi: 10.1002/jrs.v40:9
2. [2]
  (2) El-Hiti, G. A. Spectro. Lett. 1999, 32, 671. doi: 10.1080/00387019909350016
3. [3]
  (3) Pendergast,W.; Johnson, J. V.; Dickerson, S. H.; Dev, I. K.;Duch, D. S.; Ferone, R.; Hall,W. R.; Humphrey, J.; Kelly, J. M.;Wilson, D. C. J. Med. Chem. 1993, 36, 2279. doi: 10.1021/jm00068a004
4. [4]
  (4) Alagarsamy, V.; Giridhar, R.; Yadav, H. R.; Revathi, R.;Rukmani, K.; De Clercq, E. Indian J. Pharm. Sci. 2006, 68, 532.doi: 10.4103/0250-474X.27840
5. [5]
  (5) Gupta, D. P.; Ahmed, S.; Kumar, A.; Shankar, K. Indian J.Chem. 1988, 27, 1060.
6. [6]
  (6) Jatav, V.; Mishra, P.; Kashaw, S.; Stables, J. P. Eur. J. Med.Chem. 2008, 43, 135. doi: 10.1016/j.ejmech.2007.02.004
7. [7]
  (7) Joshi, V.; Chaurasia, R. P. Indian J. Chem. 1987, 26, 602.
8. [8]
  (8) Prouse, I. R. Drugs Future 1993, 18, 475.
9. [9]
  (9) Bhandari, S. V.; Deshmane, B. J.; Dangare, S. C.; re, S. T.;Raparti, V. T.; C.V. Khachane, C. V.; Sarkate, A. P.Pharmacologyonline 2008, 2, 604.
10. [10]
  (10) Azza, M. R.; Eman, E. R.; Fatma, G. E. Arch. Pharm. 2004, 337,527.
11. [11]
  (11) Fry, D.W.; Kraker, A. J.; McMichael, A.; Ambroso, L. A.;Nelson, J. M.; Leopold,W. R.; Connors, R.W.; Bridges, A. J.Science 1994, 265, 1093. doi: 10.1126/science.8066447
12. [12]
  (12) Traxler, T. M.; Furet, P.; Mett, H.; Buchdunger, E.; T. Meyer, T.;Lydon, N. J. Med. Chem. 1996, 39, 2285. doi: 10.1021/jm960118j
13. [13]
  (13) Somers, F.; Ouedrao , R.; Antoine, M. H; de Tullio, P.; Becker,B.; Fontaine, J.; Damas, J.; Dupont, L.; Ri , B.; Delarge, J.;Lebrun, P.; Pirotte, B. J. Med. Chem. 2001, 44, 2575. doi: 10.1021/jm0004648
14. [14]
  (14) Alagarsamy, V.; Dhanabal, K.; Parthiban, P.; Anjana, G.; Deepa,G.; Murugesan, B.; Rajkumar, S.; Beevi, A. J. J. Pharm.Pharmacol. 2007, 59, 669.
15. [15]
  (15) Pandey, V. K.; Tusi, S.; Tusi, Z.; Raghubir, R.; Dixit, M.; Joshi,M. N. Indian J. Chem. 2004, 43, 180.
16. [16]
  (16) Kamal, A.; Devaiah, V.; Sankarajah, N.; Reddy, K. L. Synlett2006, 16, 2609.
17. [17]
  (17) Kimber, K. M.; Yonno, L.; Hearlip, R.;Weichman, B. AgentActions 1993, 39, 677.
18. [18]
  (18) Duplantier, A. J.; Cherg, J. B. Annu. Rep. Med. Chem. 1994, 29,73.
19. [19]
  (19) Al-Sehemi, A. G.; Atkinson, R. S.; Fawcett, J.; Russell, D. R.Chem. Commun. 2000, 43.
20. [20]
  (20) Al-Sehemi, A. G.; Atkinson, R. S.; Fawcett, J.; Russell, D. R.Tetrahedron Lett. 2000, 41, 2239. doi: 10.1016/S0040-4039(00)00138-6
21. [21]
  (21) Al-Sehemi, A. G.; Atkinson, R. S.; Fawcett, J.; Russell, D. R.J. Chem. Soc. Perkin Trans. 2000, 1, 4413.
22. [22]
  (22) Al-Sehemi, A. G.; Atkinson, R. S.; Fawcett, J. J. Chem. Soc.Perkin Trans. 2002, 1, 257.
23. [23]
  (23) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03,Revision C.02; Gaussian Inc.: PittsburghWallingford, CT, 2004.
24. [24]
  (24) Irfan, A.; Al-Sehemi, A. G. J. Chem. Soc. Pak. 2012, 34, 350.
25. [25]
  (25) Head- rdon, M.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett.1988, 153, 503.
26. [26]
  (26) Frisch, M. J.; Head- rdon, M.; Pople, J. A. Chem. Phys. Lett.1990, 166, 275. doi: 10.1016/0009-2614(90)80029-D
27. [27]
  (27) Head- rdon, M.; Head- rdon, T. Chem. Phys. Lett. 1994,220, 122.
28. [28]
  (28) Saebo, S.; Almlof, J. Chem. Phys. Lett. 1989, 154, 83.
29. [29]
  (29) Irfan, A.; Al-Sehemi, A. G. J. Mol. Model. 2012, 18, 4893. doi: 10.1007/s00894-012-1488-y.
30. [30]
  (30) Zhurko, G. A.; Zhurko, D. A. ChemCraft version 1.5; 2005.available from http://www.chemcraftprog.com.
31. [31]
  (31) Stolle, K. J. Prakt. Chem. 1904, 70, 427.
32. [32]
  (32) Stolle, K. Chem. Ber. 1899, 32, 797.
33. [33]
  (33) Young, J. A. J. Am. Chem. Soc. 1962, 84, 2105. doi: 10.1021/ja00870a021
34. [34]
  (34) Stolle, K, Chem. Ber. 1912, 45, 282.
35. [35]
  (35) Sandstrom, J. Dynamic NMR Spectroscopy; Elsevier Scienceand Technology: London, 1982; p 226.
36. [36]
  (36) Al-Sehemi, A. G.; EL- gary T. M. Journal of MolecularStructure: Theochem 2009, 907, 66.
37. [37]
  (37) Al-Sehemi, A. G.; Irfan, A.; Asiri, A. M.; Ammar, Y. A. J. Mol.Struc. 2012, 1019, 130. doi: 10.1016/j.molstruc.2012.02.035
38. [38]
  (38) Arslan, H.; Florke, U.; Kulcu, N.; Binzet, G. Spectrochim. ActaA 2007, 68, 1347. doi: 10.1016/j.saa.2007.02.015
39. [39]
  (39) Al-Sehemi, A. G.; Al-Amri, R.; Irfan, A. J. Chem. Soc. Pak.2012, accepted.
40. [40]
  (40) Soni, P. L. Textbook of Inorganic Chemistry; Sultan Chand &Sons: New Delhi, 1984.
41. [41]
  (41) Foresman, J. B.; Frisch, E. Exploring Chemistry with ElectronicStructure Methods: A Guide to Using Gaussian; Gaussian:Pittsburg, PA, 1995.
42. [42]
  (42) Mayo, D.W.; Miller, F. A.; Hannah, R.W. Course Notes on theInterpretation of Infrared and Raman Spectra; Wiley & SonsInc.: Hoboken, NJ, USA, 2004.
43. [43]
  (43) Engasser, J. M.; Horvath, C. Biochem. J. 1975, 45, 43158.
44. [44]
  (44) Crane, L. G.;Wang, D.; Sears, L. M.; Heynz, B.; Carron, K.Anal. Chem. 1995, 67, 360. doi: 10.1021/ac00098a021
45. [45]
  (45) Bezzerra, A. C. S.; De Sa, E. L.; Nart, F. C. J. Phys. Chem.1997, 101, 6443. doi: 10.1021/jp9700793
46. [46]
  (46) El-Behery, M.; El-Twigry, H. Spectrochim. Acta A 2007, 66, 28.doi: 10.1016/j.saa.2006.02.017
47. [47]
  (47) Sundaraganesan, N.; Ayyappan, S.; Umamaheswari, H.; Joshua,B. D. Spectrochim. Acta A 2007, 66, 17. doi: 10.1016/j.saa.2006.02.015
48. [48]
  (48) Panicker, C. Y.; Varghese, H. T.; Ambujakshan, K. R.; Mathew,S.; Ganguli, S.; Nanda, A. K.; Alsenoy, C. V.; Mary, Y. S.J. Mol. Struct. 2010, 963, 137. doi: 10.1016/j.molstruc.2009.10.026270
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