Charge density analysis of ferulic acid: Robustness of a trifurcated C-H•••O hydrogen bond

Crystal Growth and Design

Volumn 12, Issue 12, 2012, Pages 6083-6091

  Thomas, Sajesh P ^a   Pavan, Mysore S ^a   Guru Row, Tayur N ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BOND CRITICAL POINTS; CHARGE-DENSITY ANALYSIS; FERULIC ACIDS; HYDROGEN BOND ENERGY; INTERACTION ENERGIES; INTERACTION REGION; MOLECULAR DIMERS; OXYGEN ATOM; POTENTIAL ENERGY DENSITY; WEAK HYDROGEN BOND;

DIMERS;

HYDROGEN BONDS;

EID: 84870823278     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg301211h     Document Type: Article

References (77)

1. Desiraju, G. R.; Vittal, J. J.; Ramanan, A. Crystal Engineering: A Textbook; World Scientific Publishing Company Incorporated: Singapore, 2012.
2. Desiraju, G.; Steiner, T. Oxford University Press: Oxford, 1999; Vol. 9, p 507.
3. Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 285, 170-173
4. Espinosa, E.; Souhassou, M.; Lachekar, H.; Lecomte, C. Acta Crystallogr., Sect. B: Struct. Sci 1999, 55, 563-572
5. Espinosa, E.; Lecomte, C.; Molins, E. Chem. Phys. Lett. 1999, 300, 745-748
6. Espinosa, E.; Molins, E. J. Chem. Phys. 2000, 113, 5686-5694
7. Espinosa, E.; Alkorta, I.; Rozas, I.; Elguero, J.; Molins, E. Chem. Phys. Lett. 2001, 336, 457-461
8. Espinosa, E.; Alkorta, I.; Elguero, J.; Molins, E. J. Chem. Phys. 2002, 117, 5529-5542
9. Mallinson, P. R.; Smith, G. T.; Wilson, C. C.; Grech, E.; Wozniak, K. J. Am. Chem. Soc. 2003, 125, 4259-4270
10. Dominiak, P. M.; Makal, A.; Mallinson, P. R.; Trzcinska, K.; Eilmes, J.; Grech, E.; Chruszcz, M.; Minor, W.; Woźniak, K. Chem.-Eur. J. 2006, 12, 1941-1949
11. Desiraju, G. R. Angew. Chem. Int. Ed. Eng. 1995, 34, 2311-2327
12. Desiraju, G. R. Angew. Chem., Int. Ed. 2007, 46, 8342-8356
13. Dunitz, J. D.; Gavezzotti, A. Angew. Chem., Int. Ed. 2005, 44, 1766-1787
14. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1994.
15. Leonard, G. A.; McAuley-Hecht, K.; Brown, T.; Hunter, W. N. Acta Crystallogr. Sect. D 1995, 51, 136-139
16. Mandel-Gutfreund, Y.; Margalit, H.; Jernigan, R. L.; Zhurkin, V. B. J. Mol. Biol. 1998, 277, 1129-1140
17. Steiner, T.; Saenger, W. J. Am. Chem. Soc. 1993, 115, 4540-4547
18. Derewenda, Z. S.; Derewenda, U.; Kobos, P. M. J. Mol. Biol. 1994, 241, 83-93
19. Paton, R. S.; Goodman, J. M. Org. Lett. 2006, 8, 4299-4302
20. Corey, E. J.; Rohde, J. J.; Fischer, A.; Azimioara, M. D. Tetrahedron Lett. 1997, 38, 33-36
21. Jones, C. R.; Baruah, P. K.; Thompson, A. L.; Scheiner, S.; Smith, M. D. J. Am. Chem. Soc. 2012, 134, 12064-12071
22. Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296
23. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76
24. Steiner, T. Chem. Commun. 1997, 727-734
25. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997; Vol. 12.
26. Nagawa, Y.; Yamagaki, T.; Nakanishi, H.; Nakagawa, M.; Tezuka, T. Tetrahedron Lett. 1998, 39, 1393-1396
27. Qian, W.; Krimm, S. J. Phys. Chem. A 2002, 106, 6628-6636
28. Koritsanszky, T. S.; Coppens, P. Chem. Rev. 2001, 101, 1583-1628
29. Abramov, Y. A.; Volkov, A.; Wu, G.; Coppens, P. Acta Crystallogr., Sect. A: Found. Crystallogr. 2000, 56, 585-591
30. Sosa, G. L.; Peruchena, N.; Contreras, R. H.; Castro, E. A. J. Mol. Struct.: THEOCHEM 1997, 401, 77-85
31. Lo Presti, L.; Soave, R.; Destro, R. J. Phys. Chem. B 2006, 110, 6405-6414
32. Woźniak, K.; Mallinson, P. R.; Wilson, C. C.; Hovestreydt, E.; Grech, E. J. Phys. Chem. A 2002, 106, 6897-6903
33. Castellano, R. K. Curr. Org. Chem 2004, 8, 845-865
34. Yang, H.; Craven, B. Acta Crystallogr. Sect. B: Struct. Sci. 1998, 54, 912-920
35. Mallinson, P. R.; Woźniak, K.; Smith, C. T.; McCormack, K. L. J. Am. Chem. Soc. 1997, 119, 11502-11509
36. Munshi, P.; Venugopala, K. N.; Jayashree, B. S.; Guru Row, T. N. Cryst. Growth Des. 2004, 4, 1105-1107
37. Munshi, P.; Guru Row, T. N. Acta Crystallogr., Sect. B: Struct. Sci 2006, 62, 612-626
38. Kubicki, M.; Borowiak, T.; Dutkiewicz, G.; Souhassou, M.; Jelsch, C.; Lecomte, C. J. Phys. Chem. B 2002, 106, 3706-3714
39. Gatti, C.; May, E.; Destro, R.; Cargnoni, F. J. Phys. Chem. A 2002, 106, 2707-2720
40. Desiraju, G. R.; Kashino, S.; Coombs, M. M.; Glusker, J. P. Acta Crystallogr., Sect. B: Struct. Sci 1993, 49, 880-892
41. Manoj, K.; Gonnade, R. G.; Shashidhar, M. S.; Bhadbhade, M. M. CrystEngComm 2012, 14, 1716-1722
42. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, U.K., 1994.
43. Koch, U.; Popelier, P. L. A. J. Phys. Chem. 1995, 99, 9747-9754
44. Vargas, R.; Garza, J.; Dixon, D. A.; Hay, B. P. J. Am. Chem. Soc. 2000, 122, 4750-4755
45. Munshi, P.; Guru Row, T. N. J. Phys. Chem. A 2004, 109, 659-672
46. Scheiner, S.; Kar, T.; Gu, Y. J. Biol. Chem. 2001, 276, 9832-9837
47. Park, H.; Yoon, J.; Seok, C. J. Phys. Chem. B 2007, 112, 1041-1048
48. Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449
49. Pacheco-Palencia, L. A.; Mertens-Talcott, S.; Talcott, S. T. J. Agric. Food. Chem. 2008, 56, 4631-4636
50. Valentão, P.; Fernandes, E.; Carvalho, F.; Andrade, P. B.; Seabra, R. M.; Bastos, M. L. J. Agric. Food. Chem. 2001, 49, 3476-3479
51. AgilentTechnologies; 171.35.21 ed.; Agilent Technologies Ltd.: Yarnton,Oxfordshire, England, 2011.
52. Blessing, R. J. Appl. Crystallogr. 1997, 30, 421-426
53. Sheldrick, G. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112-122
54. Farrugia, L. J. Appl. Crystallogr. 2012, 45, 849-854
55. Hansen, N. K.; Coppens, P. Acta Crystallogr., Sect. A: Found. Crystallogr. 1978, 34, 909-921
56. Volkov, A.; Macchi, P.; Farrugia, L. J.; Gatti, C.; Mallinson, P. R.; Richter, T.; Koritsanszky, T. S.; Version 5.34; University at Buffalo, State University of New York: New York, 2006.
57. Su, Z.; Coppens, P. Acta Crystallogr., Sect. A: Found. Crystallogr. 1998, 54, 357
58. Hoser, A. A.; Dominiak, P. M.; Wozniak, K. Acta Crystallogr., Sect. A: Found. Crystallogr. 2009, 65, 300-311
59. Allen, F. H.; Bruno, I. J. Acta Crystallogr., Sect. B: Struct. Sci 2010, 66, 380-386
60. Madsen, A. J. Appl. Crystallogr. 2006, 39, 757-758
61. Munshi, P.; Madsen, A. O.; Spackman, M. A.; Larsen, S.; Destro, R. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 465-475
62. Volkov, A.; Gatti, C.; Abramov, Y.; Coppens, P. Acta Crystallogr., Sect. A: Found. Crystallogr. 2000, 56, 252-258
63. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
64. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
65. Schafer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577
66. Peintinger, M. F.; Oliveira, D. V.; Bredow, T. J. Comput. Chem. 2012, 10.1002/jcc.23153
67. Dovesi, R.; Saunders, V. R.; Roetti, C.; Orlando, R.; Zicovich-Wilson, C. M.; Pascale, F.; Civalleri, B.; Doll, K.; Harrison, N. M.; Bush, I. J.; D'Arco, P.; Llunell, M.; University of Torino: Torino, 2009.
68. Nethaji, M.; Pattabhi, V.; Desiraju, G. R. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1988, 44, 275-277
69. Meindl, K.; Henn, J. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 404-418
70. Hirshfeld, F. Acta Crystallogr., Sect. A: Found. Crystallogr. 1976, 32, 239-244
71. Spackman, M. A.; Munshi, P.; Dittrich, B. ChemPhysChem 2007, 8, 2051-2063
72. Hübschle, C. B.; Dittrich, B. J. Appl. Crystallogr. 2011, 44, 238-240
73. Volkov, A.; Koritsanszky, T.; Coppens, P. Chem. Phys. Lett. 2004, 391, 170-175
74. Williams, D. E.; Cox, S. R. Acta Crystallogr., Sect. B: Struct. Sci 1984, 40, 404-417
75. Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2382-2426
76. Abramov, Y. Acta Crystallogr., Sect. A: Found. Crystallogr. 1997, 53, 264-272
77. Coppens, P.; Abramov, Y.; Carducci, M.; Korjov, B.; Novozhilova, I.; Alhambra, C.; Pressprich, M. R. J. Am. Chem. Soc. 1999, 121, 2585-2593