Syntheses, structural characterization, and DPPH radical scavenging activity of cocrystals of caffeine with 1- and 2-naphthoxyacetic acids

Journal of Molecular Structure

Volumn 1035, Issue , 2013, Pages 476-482

  Suresh Kumar, G S ^a   Seethalakshmi, P G ^b   Sumathi, D ^a   Bhuvanesh, N ^c   Kumaresan, S ^a  

^a MANONMANIAM SUNDARANAR UNIVERSITY   (India)

^b APC Mahalaxmi College for Women   (India)

^c TEXAS A AND M UNIVERSITY   (United States)

Author keywords

Caffeine; Cocrystal; Density functional theory; DPPH radical scavenging activity; Naphthoxyacetic acid; X ray crystallography

Indexed keywords

CO-CRYSTALS; CRYSTAL PACKINGS; DPPH RADICAL SCAVENGING ACTIVITIES; FTIR; GROWN CRYSTALS; POWDER X RAY DIFFRACTION; SINGLE CRYSTAL X-RAY DIFFRACTION ANALYSIS; SLOW EVAPORATION TECHNIQUES; SOLVENT FREE; SPACE GROUPS; STACKING INTERACTION; STRUCTURAL CHARACTERIZATION; TGA/DTA ANALYSIS; THERMAL BEHAVIORS;

CAFFEINE; DENSITY FUNCTIONAL THEORY; FUNCTIONAL GROUPS; HYDROGEN BONDS; SPECTRUM ANALYSIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION ANALYSIS;

SINGLE CRYSTALS;

EID: 84872592397     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2012.12.022     Document Type: Article

References (60)

1. T.W. Panunto, Z.U. Lipkowska, R. Johnson, and M.C. Etter J. Am. Chem. Soc. 109 1987 7786 7797
2. N. Shan, and M.J. Zaworotko Drug Discovery Today 13 3 2008 440
3. M.C. Etter J. Phys. Chem. 95 1991 4601 4610
4. M.C. Etter, Z.U. Lipkowska, S. Mohammad Zia-Ebrahimi, and T.W. Panunto J. Am. Chem. Soc. 112 1990 8415 8426
5. M.C. Etter, S.M. Reutzel, and C.G. Choo J. Am. Chem. Soc. 115 1993 4411 4412
6. F. Wöhler Untersuchungen uber das Chinon Annalen 51 1844 153
7. A.R. Ling, and J.L. Baker J. Chem. Soc. 63 1893 1314 1327
8. G.R. Desiraju Cryst. Eng. Commun. 5 2003 466 467
9. S.H. Lapidus, P.W. Stephens, K.K. Arora, T.R. Shattock, and M.J. Zaworotko Cryst. Growth Des. 10 10 2010 4630
10. J.D. Dunitz Cryst. Eng. Commun. 5 2003 506-506
11. W. Jones MRS Bull. 31 2006 875 879
12. L.H. Thomas, A.J. Florenceb, and C.C. Wilson New J. Chem. 33 2009 2486 2490
13. W. Jones Organic Molecular Solids: Properties and Applications W. Jones, 1997 CRC Press New York 177
14. V.R. Hathwar, R. Pal, and T.N. Guru Row Cryst. Growth Des. 10 8 2010 3306
15. A.D. Bond, and W. Jones Supramolecular Organisation and Materials Design W. Jones, C.N.R. Rao, 2002 Cambridge University Press Cambridge 391
16. J.I. Arenas-Garcia, D. Herrera-Ruiz, K. Mondragon-Vasquez, H. Morales-Rojas, and H. Hopfl Cryst. Growth Des. 10 8 2010 3732
17. J.L. Atwood, J.E.D. Davies, D.D. MacNicol, and F. Vogtle Comprehensive Supramolecular Chemistry 1996 Pergamon Oxford
18. J.F. Remenar, S.L. Morissette, M.L. Peterson, B. Moulton, J.M. MacPhee, H.R. Guzmán, and Ö. Almarsson J. Am. Chem. Soc. 125 2003 8456
19. M.L. Cheney, D.R. Weyna, N. Shan, M. Hanna, L. Wojtas, and M.J. Zaworotko Cryst. Growth Des. 10 10 2010 4401
20. A. Sarfraz, A. Simo, R. Fenger, W. Christen, K. Rademann, U. Panne, and F. Emmerling Cryst. Growth Des. 12 2012 583 588
21. O. Bolton, L.R. Simke, P.F. Pagoria, and A.J. Matzger Cryst. Growth Des. 12 2012 4311 4314
22. R.D. Bailey Walsh, M.W. Bradner, S. Fleischman, L.A. Morales, B. Moulton, N.R. Hornedo, and M.J. Zaworotko Chem. Commun. 2003 186
23. L. Rajput, G. Mukherjee, K. Biradha, Cryst. Growth Des. (2012) dx.doi.org/10.1021/cg301272h.
24. A. Mercer, and J. Trotter Acta Crystallogr. B34 1978 450 453
25. A. Chandramohan, D. Gayathri, D. Velmurugan, K. Ravikumar, and M.A. Kandhaswamy Acta Crystallogr. E63 2007 2495 2496
26. S. Aitipamula, P.S. Chow, and R.B.H. Tan CrystEngComm 14 2012 2381 2385
27. T. Friscic, D.G. Reid, G.M. Day, M.J. Duer, and W. Jones Cryst. Growth Des. 11 2011 972
28. G. He, P.S. Chow, and R.B.H. Tan Cryst. Growth Des. 10 8 2010 3763
29. A.V. Trask, W.D.S. Motherwell, and W. Jones Cryst. Growth Des. 5 3 2005 1013
30. A.V. Trask, W.D.S. Motherwell, and W. Jones Cryst Growth Des 5 2005 1013 1021
31. G.S. Suresh Kumar, P.G. Seethalakshmi, N. Bhuvanesh, and S. Kumaresan J. Mol. Str. 1034 2013 302 309
32. T.A.H. William, P. Ramadevi, P.G. Seethalakshmi, and S. Kumaresan Acta Cryst. E63 2007 o3911
33. P.G. Seethalakshmi, P. Ramadevi, S. Kumaresan, and T.A.H. William Acta Cryst. E63 2007 o4837
34. S. Kumaresan, P.G. Seethalakshmi, P. Kumaradhas, and B. Devipriya J. Mol. Struct. 1032 2013 169 175
35. S. Kumaresan, M. Indrani, R. Ramasubramanian, R. Suba, P.E. Karthik, S. Athaven, and F.R. Fronzcek Int. J. Curr. Chem. 1 3 2010 163 174
36. APEX2 "Program for Data Collection on Area Detectors" BRUKER AXS Inc., 5465 East Cheryl Parkway, Madison, WI 53711-5373, USA.
37. SADABS, Sheldrick, G.M., "Program for Absorption Correction of Areadetector Frames", BRUKER AXS Inc., 5465 East Cheryl Parkway, Madison, WI 53711-5373, USA.
38. G.M. Sheldrick, Acta Cryst. A64 (2008) 112-122. XS, BRUKER AXS Inc., 5465 East Cheryl Parkway, Madison, WI 53711-5373, USA.
39. O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard, and H. Puschmann J. Appl. Cryst. 42 2009 339 341
40. A.L. Spek Appl. Cryst. 36 2003 7
41. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B37 1993 5612
42. A.D. Becke J. Chem. Phys. 98 1993 5648
43. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford C.
44. B.S. Furniss, A.J. Hannaford, P.W.G. Smith, and R. Austin Vogel's Textbook of Practical Organic Chemistry, V edition 1989 Longman Scientific & Technical
45. G.S. Suresh Kumar, and S. Kumaresan J. Chem. Sci. 124 4 2012 857
46. G.S. Suresh Kumar, S. Kumaresan, A. Antony Muthu Prabu, and P.G. Seethalakshmi Spectrochimica Acta A 101 2013 254 263
47. K. Ramalakshmi, L. Jagan Mohan Rao, Y.T. Ishikawa, and M. Goto Food Chem. 115 2009 79
48. M.H. Abdille, R.P. Singh, G.K. Jayaprakasha, and B.S. Jena Food Chem. 90 2005 891
49. D.K. Bucar, R.F. Henry, X. Lau, R.W. Duerst, T.B. Borchardt, L.R. Mac Gillivray, and G.G. Zhang Mol. Pharm. 4 3 2007 339
50. M.C. Etter, J.C. MacDonald, and J. Bernstein Acta Cryst. B46 1990 256 262
51. M.C. Etter Acc. Chem. Res. 23 1990 120 126
52. J. Bernstein, R.E. Davis, L. Shimoni, and N.L. Chang Angew. Chem. Int. Ed. Engl. 34 1995 1555 1573
53. D.K. Bucar, R.F. Henry, X. Lou, R.W. Duerst, T.B. Borchardt, L.R. MacGillivray, and G.G.Z. Zhang Mol. Pharm. 4 3 2007 339 346
54. J.B. Lambert, H.F. Shurvell, D.A. Lightner, and R.G. Cooks Organic Structural Spectroscopy 1998 Prentice Hall New Jersey
55. R.M. Silverstein, G.C. Bassler, and T.C. Morrill Spectrometric Identification of Organic Compounds fifth ed. 1991 John Wiley & Sons New York
56. P. Pretsch, P. Buhlman, and C. Affolter Structure Determination of Organic Compounds Tables of Spectral Data 2000 Springer Berlin
57. A.V. Trask Cryst. Growth Des. 5 6 2005 2233 2241
58. S. Karki, L. Fabian, T. Friscic, and W. Jones Org. Lett. 9 16 2007 3133 3136
59. A.V. Trask, W.D. Samuel Motherwell, and W. Jones Chem. Commun. 2004 890 891
60. A.K. Mahapatra, J. Roy, P. Sahoo, S.K. Mukhopadhyay, A.R. Mukhopadhay, and D. Mandal Biorg. Med. Chem. Lett. 22 2012 5379