A facile method to determine the absolute structure of achiral molecules: Supramolecular-tilt structures

Chemistry - A European Journal

Volumn 19, Issue 19, 2013, Pages 6044-6051

  Tejedor, Rosa María ^a   Uriel, Santiago ^b   Graus, Sara ^b   Sierra, Teresa ^b,c   Serrano, José Luis ^b   Claramunt, Rosa M ^d   López, Concepción ^d   Pérez Torralba, Marta ^d   Alkorta, Ibon ^e   Elguero, José ^e  

^a CENTRO UNIVERSITARIO DE LA DEFENSA   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

^c Instituto de Ciencia de Materiales de Aragón   (Spain)

^d UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

^e INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

chirality; enantiomeric excess; noncovalent interactions; vibrational circular dichroism; X ray diffraction

Indexed keywords

ABSOLUTE CONFIGURATION; ABSOLUTE STRUCTURE; CHIRAL COMPOUNDS; CHIRAL STRUCTURES; ENANTIOMERIC EXCESS; NON-COVALENT INTERACTION; VIBRATIONAL CIRCULAR DICHROISM; VIBRATIONAL CIRCULAR DICHROISM SPECTRUM;

CHIRALITY; DICHROISM; ENANTIOMERS; IONS; X RAY DIFFRACTION;

STEREOCHEMISTRY;

3,5 DIMETHYL 4 NITROPYRAZOLE; 3,5-DIMETHYL-4-NITROPYRAZOLE; 4 HYDROXY 4 (P METHOXY PHENYL)CYCLOHEXANONEETHYLENE KETAL; 4 METHOXY 4 (P METHOXYPHENYL)CYCLOHEXANONEETHYLENE KETAL; 4-HYDROXY-4-(P-METHOXY PHENYL)CYCLOHEXANONEETHYLENE KETAL; 4-METHOXY-4-(P-METHOXYPHENYL)CYCLOHEXANONEETHYLENE KETAL; CYCLOHEXANONE DERIVATIVE; PYRAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; EQUIPMENT; STEREOISOMERISM; X RAY DIFFRACTION;

CIRCULAR DICHROISM; CYCLOHEXANONES; MOLECULAR STRUCTURE; PYRAZOLES; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 84877299940     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201204197     Document Type: Article

References (61)

1. G. A. Hembury, V. V. Borovkov, Y. Inoue, Chem. Rev. 2008, 108, 1-73.
2. I. Weissbuch, M. Lahav, Chem. Rev. 2011, 111, 3236-3267
3. L. Pérez-García, D. B. Amabilino, Chem. Soc. Rev. 2002, 31, 342-356
4. L. Pérez-García, D. B. Amabilino, Chem. Soc. Rev. 2007, 36, 941-967.
5. E. Pidcock, Chem. Commun. 2005, 3457-3459.
6. C. Dryzun, D. Avnir, Chem. Commun. 2012, 48, 5874-5876.
7. T. Matsuura, H. Koshima, J. Photochem. Photobiol. C 2005, 6, 7-24.
8. B. L. Feringa, R. A. van Delden, Angew. Chem. Int. Ed. 1999, 38, 3418-3438
9. M. Vestergren, J. Eriksson, M. Hakansson, Chem. Eur. J. 2003, 9, 4678-4686
10. B. S. Green, M. Lahav, D. Rabinovich, Acc. Chem. Res. 1979, 12, 191-197.
11. T. Kawasaki, K. Jo, H. Igarashi, I. Sato, M. Nagano, H. Koshima, K. Soai, Angew. Chem. 2005, 117, 2834-2837
12. Angew. Chem. Int. Ed. 2005, 44, 2774-2777
13. T. Kawasaki, M. Nakaoda, N. Kaito, T. Sasagawa, K. Soai, Orig. Life Evol. Biosph. 2010, 40, 65-78
14. T. Kawasaki, K. Suzuki, Y. Hakoda, K. Soai, Angew. Chem. 2008, 120, 506-509
15. Angew. Chem. Int. Ed. 2008, 47, 496-499
16. C. Viedma, Phys. Rev. Lett. 2005, 94, 65504-65507.
17. L. A. Nafie, J. C. Cheng, P. J. Stephens, J. Am. Chem. Soc. 1975, 97, 3842-3843
18. L. A. Nafie, T. A. Keiderling, P. J. Stephens, J. Am. Chem. Soc. 1976, 98, 2715-2723
19. A. Aamouche, F. J. Devlin, P. J. Stephens, J. Am. Chem. Soc. 2000, 122, 2346-2354
20. P. J. Stephens, F. J. Devlin, J.-J. Pan, Chirality 2008, 20, 643-663
21. P. J. Stephens, J. J. Pan, F. J. Devlin, K. Krohn, T. Kurtan, J. Org. Chem. 2007, 72, 3521-3536.
22. Z. Dauter, Acta Crystallogr. Sect. D 2006, 62, 867-876
23. H. D. Flack, U. Shmueli, Acta Crystallogr. Sect. A 2007, 63, 257-265
24. H. D. Flack, G. Bernardinelli, D. A. Clemente, A. Linden, A. L. Spek, Acta Crystallogr. Sect. B 2006, 62, 695-701.
25. R. W. W. Hooft, L. H. Straver, A. L. Spek, J. Appl. Crystallogr. 2008, 41, 96-103
26. A. L. Thompson, D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712-717
27. R. W. W. Hooft, L. H. Straver, A. L. Spek, J. Appl. Crystallogr. 2010, 43, 665-668
28. A. L. Thompson, D. J. Watkin, J. Appl. Crystallogr. 2011, 44, 1017-1022.
29. D. Rabinovich, H. Hope, Acta Crystallogr. 1980, A36, 670-678
30. K. Ishikawa, M. Tanaka, T. Suzuki, A. Sekine, T. Kawasaki, K. Soai, M. Shiro, M. Lahav, T. Asahi, Chem. Commun. 2012, 48, 6031-6033.
31. H. D. Flack, G. Bernardinelli, J. Appl. Crystallogr. 2000, 33, 1143-1148.
32. S. Graus, R. M. Tejedor, S. Uriel, J. L. Serrano, I. Alkorta, J. Elguero, J. Am. Chem. Soc. 2010, 132, 7862-7863.
33. S. Satishkumar, M. Periasamy, Tetrahedron: Asymmetry 2006, 17, 1116-1119.
34. C. Foces-Foces, F. H. Cano, J. Elguero, Gazz. Chim. Ital. 1993, 123, 477-479.
35. S. K. Kurtz, T. T. Perry, J. Appl. Phys. 1968, 39, 3798-3813
36. M. J. Prakash, T. P. Radhakrishnan, Inorg. Chem. 2006, 45, 9758-9764
37. M. J. Prakash, T. P. Radhakrishnan, Chem. Mater. 2006, 18, 2943-2949.
38. C. Kachi-Terajima, M. Ishii, T. Saito, C. Kanadani, T. Harada, R. Kuroda, Inorg. Chem. 2012, 51, 7502-7507
39. A. Hu, G. Cao, Tetrahedron: Asymmetry 2011, 22, 1332-1336.
40. W. Kaminsky, K. Claborn, B. Kahr, Chem. Soc. Rev. 2004, 33, 514-525
41. E. Gunn, R. Sours, J. B. Benedict, W. Kaminsky, B. Kahr, J. Am. Chem. Soc. 2006, 128, 14234-14235
42. K. Claborn, C. Isborn, W. Kaminsky, B. Kahr, Angew. Chem. 2008, 120, 5790-5801
43. Angew. Chem. Int. Ed. 2008, 47, 5706-5717
44. B. Kahr, J. Freudenthal, E. Gunn, Acc. Chem. Res. 2010, 43, 684-692.
45. J. J. L. González, F. P. Ureña, J. R. A. Moreno, I. Mata, E. Molins, R. M. Claramunt, C. Lopez, I. Alkorta, J. Elguero, New J. Chem. 2012, 36, 749-758.
46. P. Popelier, A. T. H. Lenstra, C. Vanalsenoy, H. J. Geise, J. Am. Chem. Soc. 1989, 111, 5658-5660
47. F. H. Allen, S. E. Harris, R. Taylor, J. Cold Reg. Eng. J. Comput. Aid. Mol. Des. 1996, 10, 247-254
48. N. W. Mitzel, D. H. Brown, S. Parsons, P. T. Brain, C. R. Pulham, D. W. H. Rankin, Angew. Chem. 1998, 110, 1767-1770
49. Angew. Chem. Int. Ed. 1998, 37, 1670-1672
50. A. Ben Fredj, S. Ben Rejeb, N. Jaidane, Z. Ben Lakhdar, J. Mol. Struct. 2000, 528, 219-235
51. A. Peeters, A. T. H. Lenstra, V. E. Van Doren, C. Van Alsenoy, J. Mol. Struct. (Theochem.) 2001, 546, 17-24
52. C. Ouvrard, S. L. Price, Cryst. Growth Des. Cryst. Grow. Des. 2004, 4, 1119-1127
53. F. Trautner, C. O. Della Vedova, R. M. Romano, H. Oberhammer, J. Mol. Struct. (Theochem.) 2006, 784, 272-275.
54. Oxford Diffraction, CrysAlis CCD 2006, Oxford Diffraction Ltd., Abingdon, England.
55. G. M. Sheldrick, Acta Crystallogr. 2008, A64, 112-122.
56. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652
57. C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789
58. P. A. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213-222.
59. Gaussian 03, Revision A1, 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, V. Bakken, 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, G. 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.
60. J. P. Merrick, D. Moran, L. Radom, J. Phys. Chem. A 2007, 111, 11683-11700
61. A. P. Scott, L. Radom, J. Phys. Chem. 1996, 100, 16502-16513.