Quantum chemical and spectroscopic investigations of 5-aminoquinoline

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Volumn 74, Issue 5, 2009, Pages 1215-1223

  Arjunan, V ^a   Mohan, S ^b   Balamourougane, P S ^b   Ravindran, P ^c  

^a Kanchi Mamunivar Centre for Post Graduate Studies   (India)

^b PRIST UNIVERSITY   (India)

^c Mahatma Gandhi Govt Arts College   (India)

Author keywords

5 Aminoquinoline; DFT; FT Raman; FTIR; NMR

Indexed keywords

CALCULATIONS; CHEMICAL ANALYSIS; CHEMICAL COMPOUNDS; CHEMICAL SHIFT; ELECTRONIC PROPERTIES; MOLECULAR VIBRATIONS; MOLECULES; NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY;

5-AMINOQUINOLINE; ABSORPTION WAVELENGTHS; FOURIER TRANSFORM INFRARED; FT-RAMAN; FTIR; NUCLEAR MAGNETIC RESONANCE CHEMICAL SHIFTS; SPECTROSCOPIC INVESTIGATIONS; VIBRATIONAL ASSIGNMENT;

FOURIER TRANSFORM INFRARED SPECTROSCOPY;

5 AMINOQUINOLINE; 5-AMINOQUINOLINE; AMINOQUINOLINE DERIVATIVE; CARBON;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; ELECTRON; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM THEORY; RAMAN SPECTROMETRY; THERMODYNAMICS; VIBRATION;

AMINOQUINOLINES; CARBON; ELECTRONS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; QUANTUM THEORY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SPECTRUM ANALYSIS, RAMAN; THERMODYNAMICS; VIBRATION;

EID: 75549090260     PISSN: 13861425     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.saa.2009.09.039     Document Type: Article

References (82)

1. L. Strekowski, J.L. Mokrosz, V.A. Honkan, A. Czarxy, M.T. Ceyla, R.L. Wydra, S.E. Patterson, R.F. Schinazi, J. Med. Chem. 34 (1991) 1739-1746.
2. K.E. Fox, Eur. Pat. Appl. Ep356, 193 (1990).
3. R. Gupta, A.K. Gupta, S. Paul, Ind. J. Chem. 37B (1998) 1211-1213.
4. D. Dube, M. Blowin, C. Brideau, Bioorg. Med. Chem. Lett. 8 (1998) 1255.
5. R. Gupta, A.K. Gupta, S. Paul, Ind. J. Chem. 39B (2000) 847-850.
6. S. Tiwari, P.M.S. Chauhan, D.P. Bhaduri, Bioorg. Med. Chem. Lett. 10 (2000) 1409-1412.
7. M. Kidwai, K.R. Bhushan, Sapra, Bioorg. Med. Chem. Lett. 8 (2000) 69-72.
8. M. Fujita, K. Ciba, Y. Tominaga, Chem. Pharm. Bull. 46 (1998) 787-791.
9. J. Zeigler, R. Linck, D.W.Wright, Curr. Med. Chem. 8 (2001) 171-189.
10. P.M.S. Chauhan, S.K. Srivastava, Curr. Med. Chem. 8 (2001) 1535-1542.
11. F.M.D. Ismail, M.J. Dascombe, P. Carr, J. Pharm. Pharmacol. 50 (1998) 483-492.
12. O. Famin, H. Krugliak, Ginsberg, Biochem. Pharmcol. 58 (1999) 59-68.
13. A. Dorn, S.R. Vippagunta, H. Matile, C. Jacquet, J.L. Vennerstrom, R.G. Ridley, Biochem. Pharmcol. 55 (1998) 727-736.
14. M.L. Go, T.L. Nigam, A.L.C. Tan, Eur. J. Pharm. Sci. 6 (1998) 19-26.
15. K.M. Khan, Z.S. Zaify, Z.A. Khan, A. Mansoor, M. Saeed, M. Schick, H.J. Kohlbau, W. Voelter, Arzneim Forsch./Drug Res. 50 (2000) 915-924.
16. L.W Deady, J. Desneres, A.J. Kaye, Bioorg. Med. Chem. 9 (2001) 445-452.
17. A. Sparatore, N. Basilico, M. Casagrande, S. Parapini, D. Taramelli, R. Brun, S. Wittlin, F. Sparatore, Bioorg. Med. Chem. Lett. 18 (2008) 3737-3740.
18. C.C. Musonda, S. Little, V. Yardley, K. Chibale, Bioorg. Med. Chem. Lett. 17 (2007) 4733-4736.
19. D.C. Warhurst, J.C. Craig, I.S. Adagu, R. Kiplin Guy, P.B. Madrid, Q.L. Fivelman, Biochem. Pharmacol. 17 (2007) 1910-1926.
20. A.W. Sweeney, C.R.B. Blackburn, K.H. Rieckmann, Am. J. Trop. Med. Hyg. 71 (2004) 187-189.
21. P.G. Bray, S.R. Hawley, S.A. Ward, Mol. Pharmacol. 50 (1996) 1551-1558.
22. G. Paragi, C. Van Alsenoy, B. Penke, Z. Timar, J. Mol. Struct.: Theochem. 666-667 (2003) 123-129.
23. K. Bahgat, A.G. Ragheb, Central Eur. J. Chem. 5 (2007) 201-220.
24. K. Arici, M. Yurdakul, S. Yurdakul, Spectrochim. Acta 61A (2005) 37-43.
25. T. Dziembowska, M. Szafran, E. Jagodzinska, I. Natkaniec, A. Pawlukoj, J.S. Kwiatkowski, J. Baran, Spectrochim. Acta 59A (2003) 2175-2189.
26. M.J. Mphahlele, A.M. El-Nahas, T.M. El-Gogary, J. Mol. Struct. 690 (2004) 151-157.
27. A.E. Ozel, Y. Buyukmurat, S. Akyuz, J. Mol. Struct. 565-566 (2001) 455-462.
28. C. Engelter, G.E. Jackson, C.L. Knight, D.A. Thornton, J. Mol. Struct. 213 (1989) 133-144.
29. L. Turker, Y. Yildirir, J. Mol. Struct.: Theochem. 676 (2004) 47-53.
30. N. Tokay, C. Ogretir, J. Mol. Struct.: Theochem. 594 (2002) 185-197.
31. A.J. Camargo, H.B. Napolitano, J. Zukerman-Schpector, J. Mol. Struct.: Theochem. 816 (2007) 145-151.
32. K. Golcuk, A. Altun, M. Kumru, Spectrochim. Acta 59A (2003) 1841-1847.
33. M.E. Vaschetto, B.A. Retamal, A.P. Monkman, J. Mol. Struct.: Theochem. 468 (1999) 209-221.
34. A.D. Becke, J. Chem. Phys. 98 (1993) 5648-5652.
35. C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37 (1988) 785-789.
36. D.A. Forsyth, A.B. Sebag, J. Am. Chem. Soc. 119 (1997) 9483-9494.
37. A.D. Becke, Phys. Rev. A 38 (1988) 3098-3100.
38. P. Hohenberg, W. Kohn, Phys. Rev. 136 (1964) B864-B871.
39. 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, 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, 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 Inc., Wallingford, CT (2004).
40. H.B. Schlegel, J. Comput. Chem. 3 (1982) 214-218.
41. E.B. Wilson Jr., J. Chem. Phys. 7 (1939) 1047-1052.
42. E.B. Wilson Jr., J. Chem. Phys. 9 (1941) 76-84.
43. E.B. Wilson Jr., J.C. Decius, P.C. Cross, Molecular Vibrations, McGraw-Hill, New York, 1955.
44. H. Fuhrer, V.B. Kartha, K.L. Kidd, P.J. Kruger, H.H. Mantsch, Computer Program for Infrared and Spectrometry, Normal Coordinate Analysis, vol. 5, National Research Council, Ottawa, Canada, 1976.
45. R. Ditchfield, J. Chem. Phys. 56 (1972) 5688-5691.
46. K. Wolinski, J.F. Hinton, P. Pulay, J. Am. Chem. Soc. 112 (1990) 8251-8260.
47. E. Runge, E.K.U. Gross, Phys. Rev. Lett. 52 (1984) 997-1000.
48. M. Petersilka, U.J. Gossmann, E.K.U. Gross, Phys. Rev. Lett. 76 (1996) 1212-1215.
49. R. Bauernschmitt, R. Ahlrichs, Chem. Phys. Lett. 256 (1996) 454-464.
50. C. Jamorski, M.E. Casida, D.R. Salahub, J. Chem. Phys. 104 (1996) 5134-5147.
51. L.V. Meervelt, M. Goethals, N. Leroux, Th. Zeegers-Huyskens, J. Phys. Org. Chem. 10 (1997) 680-686.
52. Y. Wang, S. Saebar, C.U. Pittman Jr., J. Mol. Struct.: Theochem. 281 (1993) 9l-98.
53. Z. Kisiel, O. Desyatnyk, L. Pszczolkowski, S.B. Charnley, P. Ehrenfreund, J. Mol. Spectrosc. 217 (2003) 115-122.
54. L.J. Bellamy, The Infrared Spectra of Complex Molecules, third ed., Wiley, New York, 1975.
55. G. Varsanyi, Assignments for Vibrational Spectra of Seven Hundred Benzene Derivaties, vol. I, Adam Hilger, London, 1974.
56. J.H.S. Green, D.J. Harrison, M.R. Kipps, Spectrochim. Acta 29A (1973) 1177-1189.
57. S. Mohan, N. Puviarasan, V. Ilangovan, Arab. J. Sci. Eng. 25-1A (2000) 31-34.
58. V. Arjunan, S. Mohan, S. Subramanian, B. Thimme Gowda, Spectrochim. Acta 60A (2004) 1141-1159.
59. V. Arjunan, N. Puviarasan, S. Mohan, Spectrochim. Acta 64A (2006) 233-239.
60. A. Altun, K. Golcuk, M. Kumru, J. Mol. Struct.: Theochem. 637 (2003) 155-169.
61. G. Smith, Urs. D. Wermuth, J.M.White, Acta Cryst. C64 (2008) o180-o183.
62. V. Arjunan, I. Saravanan, P. Ravindran, S. Mohan, Spectrochim. Acta 74A (2009) 375-384.
63. N. Leroux, M. Geothals, Th. Zeegers-Huyskens, Vib. Spectrosc. 9 (1995) 235-243.
64. N. Puviarasan, V. Arjunan, S. Mohan, Turk. J. Chem. 28 (2004) 53-65.
65. J.R. Durig, M.M. Bergana, H.V. Phan, J. Raman Spectrosc. 22 (1991) 141-154.
66. A.E. Frisch, A.B. Nielsen, A.J. Holder, Gaussian Inc., Pittsburgh, PA, USA, 2000.
67. H.F. Hameka, J.O. Jensen, J. Mol. Struct.: Theochem. 362 (1996) 325-330.
68. C.P. Vlahacos, H.F. Hameka, J.O. Jensen, Chem. Phys. Lett. 259 (1996) 283-286.
69. D. Zeroka, J.O. Jensen, J. Mol. Struct.: Theochem. 425 (1998) 181-192.
70. K.K. Ong, J.O. Jensen, H.F. Hameka, J. Mol. Struct.: Theochem. 459 (1999) 131-144.
71. J.O. Jensen, A. Banerjee, C.N. Merrow, D. Zeroka, J.M. Lochner, J. Mol. Struct.: Theochem. 531 (2000) 323-331.
72. J.O. Jensen, D. Zeroka, J. Mol. Struct.: Theochem. 487 (1999) 267-274.
73. H.F. Hameka, J.O. Jensen, J. Mol. Struct.: Theochem. 331 (1995) 203-214.
74. M.W. Ellzy, J.O. Jensen, H.F. Hameka, J.G. Kay, D. Zeroka, Spectrochim. Acta 57A (2001) 2417-2432.
75. S.Y. Lee, B.H. Boo, Bull. Korean Chem. Soc. 17 (1996) 760-764.
76. H.O. Kalinowski, S. Berger, S. Braun, Carbon-13 NMR spectroscopy, John Wiley & Sons, Chichester, 1988.
77. K. Pihlaja, E. Kleinpeter (Eds.), Carbon-13 chemical shifts in Structural and Sterochemical Analysis, VCH Publishers, Deerfield Beach, 1994.
78. K. Fukui, Science 218 (1982) 747-754.
79. R.H. Holm, F.A. Cotton, J. Am. Chem. Soc. 80 (1958) 5658-5663.
80. F.A. Cotton, C.W. Wilkinson, Advanced Inorganic Chemistry, third ed., Interscience Publisher, New York, 1972.
81. W. Barnum, J. Inorg. Nucl. Chem. 21 (1961) 221-237.
82. R.M. Silverstein, G.C. Bassler, T.C. Morrill, Spectrometric Identification of Organic Compounds, fifth ed., John Wiley & Sons, Inc., New York, 1981.