Transient states in [2 + 2] photodimerization of cinnamic acid: Correlation of solid-state NMR and X-ray analysis

Journal of the American Chemical Society

Volumn 130, Issue 5, 2008, Pages 1741-1748

  Khan, Mujeeb ^a   Brunklaus, Gunther ^a   Enkelmann, Volker ^a   Spiess, Hans Wolfgang ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

LOCAL SYMMETRY; PHOTODIMER; TOPOCHEMISTRY; TRANS-CINNAMIC ACID;

CORRELATION METHODS; ELECTRON ENERGY LEVELS; HYDROGEN BONDS; SOLID STATE REACTIONS; VIBRATIONAL SPECTROSCOPY; X RAY DIFFRACTION;

CARBOXYLIC ACIDS;

CARBON; CARBON 13; CINNAMIC ACID DERIVATIVE; CYCLOBUTANE; DIMER; MONOMER; TRUXILLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC FORCE MICROSCOPY; CORRELATION ANALYSIS; DIMERIZATION; ESTERIFICATION; HIGH TEMPERATURE; HYDROGEN BOND; IRRADIATION; LIGHT; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOLID STATE; SPECTROSCOPY; TEMPERATURE DEPENDENCE; VIBRATIONAL SPECTROSCOPY; X RAY ANALYSIS; X RAY DIFFRACTION;

EID: 38949172351     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0773711     Document Type: Article

References (54)

1. Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025-1074.
2. Ramamurthy, V.; Venkatesan, K. Chem. Rev. 1987, 87, 433-481.
3. Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647-678.
4. McBride, J. M.; Segmuller, B. E.; Hollingsworth, M.; Mills, D. E.; Weber, B. A. Science 1986, 234, 830-835.
5. Tomislav, F.; MacGillivray, L. R. Z. Kristallogr. 2005, 220, 351-363.
6. Desiraju, G. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311-2327.
7. Schmidt, G. M. J. J. Chem. Soc. 1964, 2014-2021.
8. Ghosh, M.; Chakrabarti, S.; Misra, T. N. J. Raman Spectrosc. 1998, 29, 263-267.
9. (b) Atkinson, S. D. M.; Almond, M. J.; Bowmaker, G. A.; Drew, M. G. B.; Feltham, E. J.; Hollins, P.; Jenkins, S. L.; Wiltshire, K. S. J. Chem. Soc., Perkin Trans. 2 2002, 9, 1533-1537.
10. (c) Davaasambuu, J.; Busse, G.; Techert, S. J. Phys. Chem. A 2006, 110, 3261-3265.
11. (d) Jenkins, S. L.; Almond, M. J.; Atkinson, S. D. M.; Drew, M. G. B.; Hollins, P.; Mortimore, J. L.; Tobin, M. J. J. Mol. Struct. 2006, 786, 220-226.
12. Kaupp, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 592-595.
13. (b) Kaupp, G. Angew. Chem. 1992, 104, 606-609.
14. Samantha, D. M.; Matthew, J. A.; Bruneel, J.; Amdrew, G.; Hollins, P.; Mascetti, J. Spectrochim. Acta 2000, A56, 2423-2430.
15. Enkelmann, V.; Wegner, G.; Novak, K. J. Am. Chem. Soc. 1993, 115, 10390-10391.
16. Abdelmoty, I.; Buchholz, V.; Di, L.; Enkelmann, V.; Wegner, G.; Foxman, B. M. Cryst. Growth Des. 2005, 17, 2210-2217.
17. Stitchell, S. G.; Harris, K. D. M.; Aliev, A. E. Struct. Chem. 1994, 5, 327-333.
18. Hilgeroth, A.; Hempel, G.; Baumeister, U.; Reichert, D. Solid State Nucl. Magn. Reson. 1999, 13, 231-243.
19. Bertmer, M.; Nieuwendaal, R. C.; Barnes, A. B.; Hayes, S. E. J. Phys. Chem. B 2006, 110, 6270-6273.
20. Harris, K. D. M.; Thomas, J. M. J. Solid State Chem. 1991, 94, 197-205.
21. Brown, S. P.; Spiess, H. W. Chem. Rev. 2001, 101, 4125-4155.
22. (b) Harris, R. K. Solid State Sci. 2004, 6, 1025-1037.
23. Harris, K. D. M.; Cheung, E. Y. Chem. Soc. Rev. 2004, 33, 526-538.
24. Brown, S. P. Prog. Nucl. Magn. Reson. Spectrosc. 2007, 50, 199-251.
25. Harris, R. K. Solid State Sci. 2004, 6, 1025-1037.
26. Harris, R. K. The Analyst 2006, 131, 351-373.
27. Schilf, W.; Kamieńsky, B.; Szady-Chełmieniecka, A.; Grech E. J. Mol. Struct. 2004, 700, 105-108.
28. Gobetto, R.; Nervi, C.; Chierotti, M. R.; Braga, D.; Maini, L.; Harris, K. R.; Hodgkinson, P. Chem. - Eur. J. 2005, 11, 7461-7471.
29. (a) Li, S.; Zheng, S.; Su, Y.; Zhang, H.; Chen, L.; Yang, J.; Ye, C.; Deng, F. J. Am. Chem. Soc. 2007, 129, 11161-11171.
30. (b) Yates, J. R.; Pham, T. N.; Pickard, C. J.; Mauri, F.; Amando, A. M.; Gil, A. M.; Brown, S. P. J. Am. Chem. Soc. 2005, 127, 10216-10220.
31. (c) Riedel, K.; Leppert, J.; Ohlenschlaeger, O.; Goerlach, M.; Ramachandran, R. J. Biomol. NMR 2005, 31, 331-336.
32. (d) Brus, J.; Dybal, J. Macromol. 2002, 35, 10038-10047.
33. (e) Brown, S. P.; Zhu, X. X.; Saalwaechter, K.; Spiess, H. W. J. Am. Chem. Soc. 2001, 123, 4275-4285.
34. (f) Schnell, I.; Brown, S. P.; Low, H. Y.; Ishida, H.; Spiess, H. W. J. Am. Chem. Soc. 1998, 120, 11784-11795.
35. (a) Fyfe, C. A; Brouwer, D. H.; Lewis, A. R.; Villaescusa, L. A.; Morris, R. E. J. Am. Chem. Soc. 2002, 124, 7770-7778.
36. (b) Liu, H.; Roger, M.; Hanson, J. C.; Grey, C. P.; Martin, J. D. J. Am. Chem. Soc. 2001, 123, 7564-7573.
37. (c) Grey, C. P.; Poshni, F. I.; Gualtieri; A. F.; Norby, P.; Hanson, J. C.; Corbin, D. R. J. Am. Chem. Soc. 1997, 119, 1981-1989.
38. (d) Schaller, T.; Buechele, U. P.; Klaerner, F. G.; Blaeser, D.; Boese, R.; Brown, S. P.; Spiess, H. W. J. Am. Chem. Soc. 2007, 129, 1293-1303.
39. Morkombe, C. R.; Zilm, K. J. Magn. Reson. 2003, 162, 479-486.
40. Furo, I.; Hedin, N. J. Magn. Reson. 2001, 152, 214-216.
41. (a) Becke, A. D. Phys. Rev. 1988, A38, 3098-3100.
42. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, A37, 785-789.
43. Krishnan, R.; Binkley, J. S.; Seger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654.
44. Frisch, M. J., et al. Gaussian 98, revision A.7; Gaussian Inc.: Pittsburgh, PA, 1998.
45. Leiserowitz, L. Acta Crystallogr. 1976, B32, 775-802.
46. Miyazawa, T.; Pitzer, K. S. J. Am. Chem. Soc. 1959, 81 (1), 74-79.
47. Cohen, M. C.; Schmidt, G. M. J.; Sonntag, F. I. J. Chem. Soc. 1964, 2000-2013.
48. Graf, F.; Meyer, R.; Ernst, R. R. J. Chem. Phys. 1981, 75, 2914-2918.
49. Meier, B. H.; Graf, F.; Ernst, R. R. J. Chem. Phys. 1982, 76, 767-774.
50. Stoeckli, A.; Furrer, A. Physica 1986, 136B, 161-164.
51. Skinner, J. L.; Trommsdorff, H. P. J. Chem. Phys. 1988, 89, 897-907.
52. Horsewill, A. J.; Aibout, A. J. Phys.: Condens. Matter 1989, 1, 9609-9622.
53. Kalsbeek, N.; Schaumberg, K.; Larsen, S. J. Mol. Struct. 1993, 299, 155-170.
54. Mayas, L.; Plato, M.; Winscom, J.; Mobius, K. Mol. Phys. 1978, 36, 753-764.