Chiral and racemic tetramorphs of 2,6-di-t-butylditolylfuchsone

Crystal Growth and Design

Volumn 12, Issue 3, 2012, Pages 1613-1625

  Nath, Naba K ^a   Nilapwar, Sanjay ^b   Nangia, Ashwini ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ATROPISOMERISM; BENZOQUINONES; CENTROSYMMETRIC; SPACE GROUPS; STERIC REPULSIONS; THERMAL MICROSCOPY;

CHIRALITY; CIRCULAR DICHROISM SPECTROSCOPY; CRYSTAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; ENANTIOMERS; PHASE TRANSITIONS; X RAY DIFFRACTION;

STEREOCHEMISTRY;

EID: 84857990807     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg201652h     Document Type: Article

References (61)

1. Jacques, J., Collet, A., and Wilen, S. H. Enantiomers, Racemates, and Resolutions; Wiley: New York, 1981.
2. Sephton, M. A.; Emerson, C. R.; Zakharov, L. N.; Blakemore, P. R. Chem. Commun. 2010, 46, 2094-2096
3. Collet, A.; Brienne, M.-J.; Jacques, J. Chem. Rev. 1980, 80, 215-230
4. Pérez-García, L.; Amabilino, D. B. Chem. Soc. Rev. 2002, 31, 342-356
5. Kondepudi, D. K.; Asakura, K. Acc. Chem. Res. 2001, 34, 946-954
6. Eliel, E. L. Stereochemistry of Carbon Compounds; Tata McGraw-Hill: New Delhi, 1975.
7. Lunazzi, L.; Mancinelli, M.; Mazzanti, A. J. Org. Chem. 2008, 73, 5354-5359
8. Cunningham, I. D.; Coles, S. J.; Hursthouse, M. B. Chem. Commun. 2000, 61-62
9. Tanaka, A.; Inoue, K.; Hisaki, I.; Tohnai, N.; Miyata, M.; Matsumoto, A. Angew. Chem., Int. Ed. 2006, 45, 4142-4145
10. Sakamoto, M.; Utsumi, N.; Ando, M.; Saeki, M.; Mino, T.; Fujita, T.; Katoh, A.; Nishio, T.; Kashima, C. Angew. Chem., Int. Ed. 2003, 42, 4360-4363
11. Zhang, J.; Chen, S.; Nieto, R. A.; Wu, T.; Feng, P.; Bu, X. Angew. Chem., Int. Ed. 2010, 49, 1267-1270
12. Pidcock, E. Chem. Commun. 2005, 3457-3459
13. Matsuura, T.; Koshima, H. J. Photochem. Photobiol. C: Photochem. Rev. 2005, 6, 7-24
14. Curtin, D. Y.; Paul, I. C. Chem. Rev. 1981, 81, 525-541
15. Zyss, J.; Chemla, D. S. In Non-linear Optical Properties of Organic Molecules and Crystals; Zyss, J.; Chemla, D. S., Eds.; Academic Press: New York, 1987; Vols. 1 and 2.
16. Suzuki, T.; Fukushima, T.; Yamashita, Y.; Miyashi, T. J. Am. Chem. Soc. 1994, 116, 2793-2803
17. Sakamoto, M.; Kobaru, S.; Mino, T.; Fujita, T. Chem. Commun. 2004, 1002-1003
18. Koshima, H.; Kawanishi, H.; Nagano, M.; Yu, H.; Shiro, M.; Hosoya, T.; Uekusa, H.; Ohashi, Y. J. Org. Chem. 2005, 70, 4490-4497
19. Guijarro, A.; Yus, M. The Origin of Chirality in Nature; RSC Publishing: Cambridge, 2009.
20. Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Chem. Commun. 2000, 887-892
21. Lewis, T. W.; Paul, I. C.; Curtin, D. Y. Acta Crystallogr. 1980, B36, 70-77
22. Duesler, E. N.; Lewis, T. W.; Curtin, D. Y.; Paul, I. C. Acta Crystallogr. 1980, B36, 166-168
23. Chandran, S. K.; Nath, N. K.; Roy, S.; Nangia, A. Cryst. Growth Des. 2008, 8, 140-154
24. Nath, N. K.; Nangia, A., unpublished results.
25. Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3440-3461
26. Kalsi, P. S. Streochemistry Conformation and Mechanism; New Age International (P) Limited Publishers: New Delhi, 2008; p 149.
27. March, J. Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 4 th ed.; Wiley Interscience: New York, 1992; pp 103-104.
28. Wolf, C. Dynamic Stereochemistry of Chiral Compounds: Principles and Applications; The Royal Society of Chemistry: Cambridge, 2008; pp 53-54.
29. Nangia, A. Acc. Chem. Res. 2008, 41, 595-604
30. Flack, D. Acta Crystallogr. 1983, A39, 876-881
31. Pescitelli, G.; Pietro, S. D.; Cardellicchio, C.; Capozzi, M. A. M.; Bari, L. D. J. Org. Chem. 2010, 75, 1143-1154
32. Minguet, M.; Amabilino, D. B.; Wurst, K.; Veciana, J. J. Chem. Soc., Perkin Trans. 2001, 2, 670-676
33. Hao, H.-Q.; Liu, W.-T.; Tan, W.; Lin, Z.-J.; Tong, M. -L. CrystEngComm 2009, 11, 967-971
34. Sun, Q.; Bai, Y.; He, G.; Duan, C.; Lin, Z.; Meng, Q. Chem. Commun. 2006, 2777-2779
35. Lennartson, A.; Wiklund, T.; Håkansson, M. CrystEngComm 2007, 9, 856-859
36. Vestergren, M.; Johansson, A.; Lennartson, A.; Håkansson, M. Mendeleev Commun. 2004, 258-260
37. Lennartson, A.; Vestergren, M.; Håkansson, M. Chem.-Eur. J. 2005, 11, 1757-1762
38. Cambridge Crystallographic Data Center, www.ccdc.cam.ac.uk.
39. Hu, C.; Englert, U. Angew. Chem., Int. Ed. 2005, 44, 2281-2283
40. Avarvari, N.; Faulques, E.; Fourmigué, M. Inorg. Chem. 2001, 40, 2570-2577
41. Supriya, S.; Das, S. K. J. Am. Chem. Soc. 2007, 129, 3464-3465
42. Zhang, Y.-J.; Liu, T.; Kanegawa, S.; Sato, O. J. Am. Chem. Soc. 2009, 131, 7942-7943
43. Vittal, J. J. Coord. Chem. Rev. 2007, 251, 1781-1795
44. Kaftory, M.; Botoshansky, M.; Kapon, M.; Shteiman, V. Acta Crystallogr. 2001, B57, 791-799
45. Takahashi, H.; Ito, Y. CrystEngComm 2010, 12, 1628-1634
46. Das, D.; Engel, E.; Barbour, L. J. Chem. Commun. 2010, 46, 1676-1678
47. Görbitz, C. H. J. Phys. Chem. 2011, B115, 2447-2453
48. Atwood, J. L.; Barbour, L. J.; Jerga, A.; Schottel, B. L. Science 2002, 298, 1000-1002
49. Ostwald, W. F. Z. Phys. Chem. 1897, 22, 289-330
50. Wallach, O. Liebigs Ann. Chem. 1895, 286, 90-143
51. Brock, C. P.; Schweizer, W. B.; Dunitz, J. D. J. Am. Chem. Soc. 1991, 113, 9811-9820
52. Morimoto, M.; Kobatake, S.; Irie, M. Chem.-Eur. J. 2003, 9, 621-627
53. Kumar, V. S. S.; Addlagatta, A.; Nangia, A.; Robinson, W. T.; Broder, C. K.; Mondal, R.; Evans, I. R.; Howard, J. A. K.; Allen, F. H. Angew. Chem., Int. Ed. 2002, 41, 3848-3851
54. Parrish, D. A.; Deschamps, J. R.; Gilardi, R. D.; Butcher, R. J. Cryst. Growth Des. 2008, 8, 57-62
55. Becker, H.-D. J. Org. Chem. 1967, 32, 2131-2136
56. SAINT-Plus, version 6.45; Bruker AXS Inc.: Madison, WI, 2003.
57. Sheldrick, G. M. SADABS, Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Germany, 1997.
58. SMART (Version 5.625) and SHELX-TL (Version 6.12); Bruker AXS Inc.: Madison, WI, 2000
59. Sheldrick, G. M. SHELXS-97 and SHELXL-97; University of Göttingen, Germany, 1997.
60. Dolomanov, O. V.; Blake, A. J.; Champness, N. R.; Schröder, M. J. Appl. Crystallogr. 2003, 36, 1283-1284
61. Barbour, L. J. X-Seed, Graphical Interface to SHELX-97 and POV-Ray, University of Missouri-Columbia, Columbia, MO, 1999.