Single crystal to single crystal topochemical photoreactions: Measuring the degree of disorder in the [2 + 2] photodimerization of trans-cinnamic acid using single-crystal 13C NMR spectroscopy

Journal of Physical Chemistry B

Volumn 115, Issue 19, 2011, Pages 5785-5793

  Nieuwendaal, Ryan C ^a   Mattler, Sarah J ^a   Bertmer, Marko ^a   Hayes, Sophia E ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C (PROGRAMMING LANGUAGE); CRYSTAL ORIENTATION; GONIOMETERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOREACTIVITY; SINGLE CRYSTALS; X RAY DIFFRACTION;

ATOMIC COORDINATE; CARBON POSITION; CHEMICAL SHIFT TENSORS; CINNAMIC ACIDS; CROSS POLARIZATIONS; DEGREE OF DISORDER; NMR SPECTROSCOPY; PHOTO-IRRADIATION; PHOTODIMERIZATION; PHOTOREACTIONS; REFERENCE FRAME; SIMPSON; SINGLE CRYSTAL X-RAY DIFFRACTION; SINGLE-CRYSTAL NMR; TOPOCHEMICAL; TRANS-CINNAMIC ACID; UNIT CELLS;

CRYSTAL SYMMETRY;

EID: 79956073975     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp200952g     Document Type: Article

References (39)

1. Ito, H. Adv. Polym. Sci. 2005, 172, 37-245
2. Lendlein, L.; Jiang, H.; Juenger, O.; Langer, R. Nature 2005, 434, 879-882
3. Cohen, M. D.; Schmidt, G. M. J. J. Chem. Soc. 1964, June) 1996-2000
4. Enkelmann, V.; Wegner, G.; Novak, K.; Wagener, K. B. J. Am. Chem. Soc. 1993, 115, 10390-10391
5. Hosomi, H.; Ito, Y.; Ohba, S. Acta Crystallogr., Sect. B 2000, B56, 682-689
6. Takahashi, S.; Miura, H.; Kasai, H.; Okada, S.; Oikawa, H.; Nakanishi, H. J. Am. Chem. Soc. 2002, 124, 10944-10945
7. Ohba, S.; Ito, Y. Acta Crystallogr., Sect. B. 2003, B59, 149-155
8. Friscic, T.; MacGillivray, L. Z. Kristallogr. 2005, 200, 351-363
9. Bucar, D. K.; MacGillivray, L. R. J. Am. Chem. Soc. 2007, 129, 32-33
10. Nieuwendaal, R.; Bertmer, M.; Hayes, S. E. J. Phys. Chem. B 2008, 41, 12920-12926
11. NMR Crystallography; Harris, R. K.; Wasylishen, R. E.; Duer, M. J., Eds.; John Wiley & Sons Ltd.: West Sussex, U.K., 2009.
12. Lai, J.; Niks, D.; Wang, Y.; Domratcheva, T.; Barends, T. R. M.; Schwarz, F.; Olsen, R. A.; Elliott, D. W.; Fatmi, M. Q.; Chang, C. A.; Schlichting, I.; Dunn, M. F.; Mueller, L. J. J. Am. Chem. Soc. 2011, 133, 4-7
13. Al-Kaysi, R. O.; Dillon, R. J.; Kaiser, J. M.; Mueller, L. J.; Guirado, G.; Bardeen, C. J. Macromolecules 2007, 40, 9040-9044
14. K. W. Zilm, K. W.; Conlin, R. T.; Grant, D. M.; Michl, J. J. Am. Chem. Soc. 1978, 100, 8038-8039
15. Zilm, K. W.; Beeler, A. J.; Grant, D. M.; Michl, J.; Chou, T. C.; Allred, E. L. J. Am. Chem. Soc. 1981, 103, 2119-2120
16. Klaus, E.; Wasylishen, R. E.; Corrigan, J. F.; Taylor, N. J.; Carty, A. J.; Feindel, K. W.; Bernard, G. M. J. Am. Chem. Soc. 2002, 124, 1541-1552
17. Mitra, A. K.; Karchaudhuri, A. D.; Karchaudhuri, N. Synth. Commun. 1999, 29, 573-581
18. Ma, G.; Hayes, S. E. J. Labelled Compd. Radiopharm. 2004, 47, 895-901
19. Wright, J. D. Molecular Crystals, 1 st ed.; Cambridge University Press: Cambridge, U.K., 1987; pp 112 - 113.
20. Nieuwendaal, R. The Topochemical [2 + 2] Photocycloaddition Reaction of α- trans -cinnamic acid: A Perspective from Solid-State NMR Measurements; Ph.D. Thesis, Washington University, St. Louis, MO, March, 2008.
21. Muller, L.; Kumar, A.; Baumann, T.; Ernst, R. R. Phys. Rev. Lett. 1974, 32, 1402-1406
22. 13C dipolar coupling between nearest neighbors is 165 Hz predicted from the crystal structure internuclear distance of 3.561 Å.
23. Bak, M; Rasmussen, J. T.; Nielsen, N. C. J. Magn. Reson. 2000, 147, 296-330
24. Bak, M.; Schultz, R.; Vosegaard, T.; Nielsen, N. C. J. Magn. Reson. 2002, 154, 28-45
25. The molecular reference frame is defined in the Supporting Information.
26. Mehring, M. High-Resolution NMR in Solids; Springer-Verlag: New York, 1983.
27. These data are in the Supporting Information.
28. ii.
29. 11.
30. Grant, D. M. Chemical Shift Tensors. In Encyclopedia of Nuclear Magnetic Resonance; Grant, D. M.; Harris, R. K., Eds.; John Wiley & Sons: 1995; Vol. 2, pp 1317 - 1318.
31. Schwoerer, M.; Wolf, H. C. Organic Molecular Solids; Wiley-VCH: Weinheim, Germany, 2007.
32. Dybowski, C. R.; Gerstein, B. C.; Vaughan, R. W. J. Chem. Phys. 1977, 67, 3412-3415 and references therein
33. Stoll, M. E.; Majors, T. J. J. Magn. Reson. 1982, 46, 283-288
34. VanderHart, D. L.; Earl, W. L.; Garroway, A. N. J. Magn. Reson. 1981, 44, 361-401
35. Drain, L. E. Proc. Phys. Soc. 1962, 80, 1380-1382
36. Van Vleck, J. H. Phys. Rev. 1948, 74, 1168
37. Purcell, E. M.; Bloembergen, N.; Pound, R. V. Phys. Rev. 1946, 70, 988
38. The photoreaction was intentionally not carried out to completion for fear of breaking the crystal as was observed in our previous study.
39. 2, which is sensitive to temperature. For more details, see: Bielecki, A. J. Magn. Reson. A 1995, 116, 215-220