Structural study of the solid-state photoaddition reaction of arylidenoxindoles

Journal of Organic Chemistry

Volumn 65, Issue 11, 2000, Pages 3416-3425

  Milanesio, Marco ^a   Viterbo, Davide ^a,b   Albini, Angelo ^c   Fasani, Elisa ^c   Bianchi, Riccardo ^d   Barzaghi, Mario ^d  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF EASTERN PIEDMONT   (Italy)

^c UNIVERSITY OF PAVIA   (Italy)

^d CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIMERIZATION; ISOMERISM; PHOTOCHEMISTRY;

EID: 0034595841     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991873i     Document Type: Article

References (57)

1. Cohen, M. D.; Schmidt, G. M. J.; Sonntag, F. I. J. Chem. Soc. 1964, 2001-2013. Schmidt, G. M. J. J. Chem. Soc. 1964, 2014-2021.
2. Cohen, M. D.; Schmidt, G. M. J.; Sonntag, F. I. J. Chem. Soc. 1964, 2001-2013. Schmidt, G. M. J. J. Chem. Soc. 1964, 2014-2021.
3. Ramamurthy, V.; Venkatesan, K. Chem. Rev. 1987, 87, 433-481. Garcia-Garibay, M. A.; Constable, A. E.; Jernelius, J.; Choi, Y.; Cizmeciyan, D.; Shin, S. H. In Physical Supramolecular Chemistry; Echegoyen, L., Kaifer, A. E., Eds.; Kluwer Academic Press: Dordercht, 1996; pp 289-312. Kaupp, G. In Organic Photochemistry and Photobiology; Horspool, W. M., Song, P. S., Eds.; CRC: Boca Raton, 1995; pp 50-63.
4. Ramamurthy, V.; Venkatesan, K. Chem. Rev. 1987, 87, 433- 481. Garcia-Garibay, M. A.; Constable, A. E.; Jernelius, J.; Choi, Y.; Cizmeciyan, D.; Shin, S. H. In Physical Supramolecular Chemistry; Echegoyen, L., Kaifer, A. E., Eds.; Kluwer Academic Press: Dordercht, 1996; pp 289-312. Kaupp, G. In Organic Photochemistry and Photobiology; Horspool, W. M., Song, P. S., Eds.; CRC: Boca Raton, 1995; pp 50-63.
5. Ramamurthy, V.; Venkatesan, K. Chem. Rev. 1987, 87, 433- 481. Garcia-Garibay, M. A.; Constable, A. E.; Jernelius, J.; Choi, Y.; Cizmeciyan, D.; Shin, S. H. In Physical Supramolecular Chemistry; Echegoyen, L., Kaifer, A. E., Eds.; Kluwer Academic Press: Dordercht, 1996; pp 289-312. Kaupp, G. In Organic Photochemistry and Photobiology; Horspool, W. M., Song, P. S., Eds.; CRC: Boca Raton, 1995; pp 50-63.
6. Novak, K.; Enkelmann, V.; Wegner, G.; Wagener, K. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 1614-1616.
7. Enkelmann, V.; Wegner, G.; Novak, K.; Wagener, K. B. J. Am. Chem. Soc. 1993, 115, 10390-10391.
8. Köhler, W.; Novak, K.; Enkelmann, V. J. Chem. Phys. 1994, 101, 10474-10480.
9. Kaupp, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 592-598.
10. Intramolecular crystal state cycloadditions involving trisubtituted C=C double bonds, with the third one being a nonconjugating, usually an alkyl group, are largely known and include cases where the double bond is exo to a ring, showing that purely steric crowding is not per se a limitation. See, e.g., refs 7 and 8: Nakanishi, H.; Jones, W.; Thomas, J. M.; Hursthouse, M. B.; Motevalli, M. J. Phys. Chem. 1981, 85, 3636-3642. Jones, W.; Ramdas, S.; Theocaris, C. R.; Thomas, J. M.; Thomas, N. W. J. Phys. Chem. 1981, 85, 2594-2597. Kearsley, S. K.; Desiraju, G. R. Proc. R. Soc. London, Ser. A, 1985, 397, 157- 181. Rabinovitch, D.; Schmidt, G. M. J. J. Chem. Soc. B 1967, 144- 149. Kaupp, G.; Jostkleigrewe, E.; Hermann, H. J. Angew. Chem., Int. Ed. Engl. 1982, 21, 435-436. Chase, D. B.; Amey, R. L.; Holtje, W. G. Appl. Spectrosc. 1982, 36, 155-158. Waschen, E.; Mantsch, R., Krampity, D, Hartke, K. Liebigs Ann. Chem. 1976, 2137-2144.
11. Intramolecular crystal state cycloadditions involving trisubtituted C=C double bonds, with the third one being a nonconjugating, usually an alkyl group, are largely known and include cases where the double bond is exo to a ring, showing that purely steric crowding is not per se a limitation. See, e.g., refs 7 and 8: Nakanishi, H.; Jones, W.; Thomas, J. M.; Hursthouse, M. B.; Motevalli, M. J. Phys. Chem. 1981, 85, 3636-3642. Jones, W.; Ramdas, S.; Theocaris, C. R.; Thomas, J. M.; Thomas, N. W. J. Phys. Chem. 1981, 85, 2594-2597. Kearsley, S. K.; Desiraju, G. R. Proc. R. Soc. London, Ser. A, 1985, 397, 157- 181. Rabinovitch, D.; Schmidt, G. M. J. J. Chem. Soc. B 1967, 144- 149. Kaupp, G.; Jostkleigrewe, E.; Hermann, H. J. Angew. Chem., Int. Ed. Engl. 1982, 21, 435-436. Chase, D. B.; Amey, R. L.; Holtje, W. G. Appl. Spectrosc. 1982, 36, 155-158. Waschen, E.; Mantsch, R., Krampity, D, Hartke, K. Liebigs Ann. Chem. 1976, 2137-2144.
12. Intramolecular crystal state cycloadditions involving trisubtituted C=C double bonds, with the third one being a nonconjugating, usually an alkyl group, are largely known and include cases where the double bond is exo to a ring, showing that purely steric crowding is not per se a limitation. See, e.g., refs 7 and 8: Nakanishi, H.; Jones, W.; Thomas, J. M.; Hursthouse, M. B.; Motevalli, M. J. Phys. Chem. 1981, 85, 3636-3642. Jones, W.; Ramdas, S.; Theocaris, C. R.; Thomas, J. M.; Thomas, N. W. J. Phys. Chem. 1981, 85, 2594-2597. Kearsley, S. K.; Desiraju, G. R. Proc. R. Soc. London, Ser. A, 1985, 397, 157-181. Rabinovitch, D.; Schmidt, G. M. J. J. Chem. Soc. B 1967, 144- 149. Kaupp, G.; Jostkleigrewe, E.; Hermann, H. J. Angew. Chem., Int. Ed. Engl. 1982, 21, 435-436. Chase, D. B.; Amey, R. L.; Holtje, W. G. Appl. Spectrosc. 1982, 36, 155-158. Waschen, E.; Mantsch, R., Krampity, D, Hartke, K. Liebigs Ann. Chem. 1976, 2137-2144.
13. Intramolecular crystal state cycloadditions involving trisubtituted C=C double bonds, with the third one being a nonconjugating, usually an alkyl group, are largely known and include cases where the double bond is exo to a ring, showing that purely steric crowding is not per se a limitation. See, e.g., refs 7 and 8: Nakanishi, H.; Jones, W.; Thomas, J. M.; Hursthouse, M. B.; Motevalli, M. J. Phys. Chem. 1981, 85, 3636-3642. Jones, W.; Ramdas, S.; Theocaris, C. R.; Thomas, J. M.; Thomas, N. W. J. Phys. Chem. 1981, 85, 2594-2597. Kearsley, S. K.; Desiraju, G. R. Proc. R. Soc. London, Ser. A, 1985, 397, 157- 181. Rabinovitch, D.; Schmidt, G. M. J. J. Chem. Soc. B 1967, 144-149. Kaupp, G.; Jostkleigrewe, E.; Hermann, H. J. Angew. Chem., Int. Ed. Engl. 1982, 21, 435-436. Chase, D. B.; Amey, R. L.; Holtje, W. G. Appl. Spectrosc. 1982, 36, 155-158. Waschen, E.; Mantsch, R., Krampity, D, Hartke, K. Liebigs Ann. Chem. 1976, 2137-2144.
14. Intramolecular crystal state cycloadditions involving trisubtituted C=C double bonds, with the third one being a nonconjugating, usually an alkyl group, are largely known and include cases where the double bond is exo to a ring, showing that purely steric crowding is not per se a limitation. See, e.g., refs 7 and 8: Nakanishi, H.; Jones, W.; Thomas, J. M.; Hursthouse, M. B.; Motevalli, M. J. Phys. Chem. 1981, 85, 3636-3642. Jones, W.; Ramdas, S.; Theocaris, C. R.; Thomas, J. M.; Thomas, N. W. J. Phys. Chem. 1981, 85, 2594-2597. Kearsley, S. K.; Desiraju, G. R. Proc. R. Soc. London, Ser. A, 1985, 397, 157- 181. Rabinovitch, D.; Schmidt, G. M. J. J. Chem. Soc. B 1967, 144- 149. Kaupp, G.; Jostkleigrewe, E.; Hermann, H. J. Angew. Chem., Int. Ed. Engl. 1982, 21, 435-436. Chase, D. B.; Amey, R. L.; Holtje, W. G. Appl. Spectrosc. 1982, 36, 155-158. Waschen, E.; Mantsch, R., Krampity, D, Hartke, K. Liebigs Ann. Chem. 1976, 2137-2144.
15. Intramolecular crystal state cycloadditions involving trisubtituted C=C double bonds, with the third one being a nonconjugating, usually an alkyl group, are largely known and include cases where the double bond is exo to a ring, showing that purely steric crowding is not per se a limitation. See, e.g., refs 7 and 8: Nakanishi, H.; Jones, W.; Thomas, J. M.; Hursthouse, M. B.; Motevalli, M. J. Phys. Chem. 1981, 85, 3636-3642. Jones, W.; Ramdas, S.; Theocaris, C. R.; Thomas, J. M.; Thomas, N. W. J. Phys. Chem. 1981, 85, 2594-2597. Kearsley, S. K.; Desiraju, G. R. Proc. R. Soc. London, Ser. A, 1985, 397, 157- 181. Rabinovitch, D.; Schmidt, G. M. J. J. Chem. Soc. B 1967, 144- 149. Kaupp, G.; Jostkleigrewe, E.; Hermann, H. J. Angew. Chem., Int. Ed. Engl. 1982, 21, 435-436. Chase, D. B.; Amey, R. L.; Holtje, W. G. Appl. Spectrosc. 1982, 36, 155-158. Waschen, E.; Mantsch, R., Krampity, D, Hartke, K. Liebigs Ann. Chem. 1976, 2137-2144.
16. Intramolecular crystal state cycloadditions involving trisubtituted C=C double bonds, with the third one being a nonconjugating, usually an alkyl group, are largely known and include cases where the double bond is exo to a ring, showing that purely steric crowding is not per se a limitation. See, e.g., refs 7 and 8: Nakanishi, H.; Jones, W.; Thomas, J. M.; Hursthouse, M. B.; Motevalli, M. J. Phys. Chem. 1981, 85, 3636-3642. Jones, W.; Ramdas, S.; Theocaris, C. R.; Thomas, J. M.; Thomas, N. W. J. Phys. Chem. 1981, 85, 2594-2597. Kearsley, S. K.; Desiraju, G. R. Proc. R. Soc. London, Ser. A, 1985, 397, 157- 181. Rabinovitch, D.; Schmidt, G. M. J. J. Chem. Soc. B 1967, 144- 149. Kaupp, G.; Jostkleigrewe, E.; Hermann, H. J. Angew. Chem., Int. Ed. Engl. 1982, 21, 435-436. Chase, D. B.; Amey, R. L.; Holtje, W. G. Appl. Spectrosc. 1982, 36, 155-158. Waschen, E.; Mantsch, R., Krampity, D, Hartke, K. Liebigs Ann. Chem. 1976, 2137-2144.
17. Theocaris, C. R.; Jones, W.; Thomas, J. M.; Motevalli, M.; Horsthouse, M. B. J. Chem. Soc., Perkin Trans. 2 1984, 71-76.
18. Kuhn, H. J.; Braslavsky, S. E.; Schmidt, R. Pure Appl. Chem. 1989, 61, 187.
19. Saltiel, G.; D'Agostino, J.; Megarity, E. D.; Metts, L.; Neuberger, K. R.; Wrighton, M.; Zafiriou, O. C. Org. Photochem. 1973, 3, 1.
20. These hydrogen bond interactions were indeed found in the crystal structure of 2-benzylidenoxindole, the crystals of which had been obtained in one of our attempts at growing suitable crystals of 2b. The crystal structure will not be described here, but the data will be deposited with the Cambridge Crystallographic Data Centre, with deposition number CCDC-137079.
21. This is another case where, despite the fact that the dimer does not fit easily within the structure of the monomer, an important condition according to Kaupp's scheme, the dimerization occurs efficiently (ca 90%) as predicted topochemically, though not in a crystal to crystal way.
22. Kitaigorodski, A. I. Organic Chemical Crystallography; Consultants Bureau, 1961.
23. The calculated lattice energies for 1a and 1b tend to zero or even to positive values. This may be attributed to the known inability of the Hartree-Fock and Density Functional methods to handle weak dispersive interactions. We intend to verify this hypothesis by carrying out calculations on smaller molecular crystals.
24. Ghosh, M.; Chakrabarti, S.; Misra; T. N. J. Phys. Chem. Solids 1996, 57, 1891-1895.
25. (a) Caldwell, R. A. J. Am. Chem. Soc. 1980, 102, 4004-4007.
26. (b) Ariel, S.; Askari, S.; Scheffer, J. R.; Trotter, J.; Walsh, L. J. Am. Chem. Soc. 1984, 106, 5726-5728.
27. Vishnumurthy, K.; Guru Row, T. N.; Venkatesan, K. J. Chem. Soc., Perkin Trans. 2 1996, 1475-1478. Vishnumurthy, K.; Guru Row, T. N.; Venkatesan, K. J. Chem. Soc., Perkin Trans. 2 1997, 615-619.
28. Vishnumurthy, K.; Guru Row, T. N.; Venkatesan, K. J. Chem. Soc., Perkin Trans. 2 1996, 1475-1478. Vishnumurthy, K.; Guru Row, T. N.; Venkatesan, K. J. Chem. Soc., Perkin Trans. 2 1997, 615-619.
29. Coates, G. W.; Dunn, A. R.; Henling, L. M.; Ziller, J. W.; Lobkovsky, E. B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 3641-3649.
30. Misra, T. N.; Prasad, P. N. Chem. Phys. Lett. 1982, 85, 381-386.
31. Ghosh, U.; Misra, T. N. Bull. Chem. Soc. Jpn. 1985, 58, 2403-2406.
32. Chakrabarti, S.; Gantait, M.; Misra, T. N. Proc. Ind. Acad. Sci. (Chem. Sci.) 1990, 102, 165-172.
33. Ghosh, M.; Chakrabarti, S.; Misra, T. N. J. Phys. Chem. Solids 1997, 59, 753-757.
34. Cohen, M. D. Angew. Chem., Int. Ed. Engl. 1975, 14, 386-393.
35. Gavezzotti, A. J. Am. Chem. Soc. 1983, 105, 5220-5225.
36. Murthy, G. S.; Arjunan, P.; Venkatesan, K.; Ramamurthy, V. Tetrahedron 1987, 43, 1225-1240.
37. Marubayashi, N.; Ogawa, T.; Hamasaki, T.; Hirayama, N. J. Chem. Soc., Perkin Trans. 2 1997, 1309-1314.
38. Marubayashi, N.; Ogawa, T.; Hirayama, N. Bull. Chem. Soc. Jpn. 1998, 71, 321-327.
39. Irmgard, F.; Marx, D.; Parrinello, M. J. Phys. Chem. 1999, 103, 7341-7344.
40. Tacconi, G.; Marinone, F. Ric. Sci. 1968, 38, 1239-1244. Stanek, J.; Ryber, D. Chem. Listy 1946, 40, 173-190. Tacconi, G.; Marinone, F.; Desimoni, G. Gazz. Chim. Ital. 1971, 101, 173-182.
41. Tacconi, G.; Marinone, F. Ric. Sci. 1968, 38, 1239-1244. Stanek, J.; Ryber, D. Chem. Listy 1946, 40, 173-190. Tacconi, G.; Marinone, F.; Desimoni, G. Gazz. Chim. Ital. 1971, 101, 173-182.
42. Tacconi, G.; Marinone, F. Ric. Sci. 1968, 38, 1239-1244. Stanek, J.; Ryber, D. Chem. Listy 1946, 40, 173-190. Tacconi, G.; Marinone, F.; Desimoni, G. Gazz. Chim. Ital. 1971, 101, 173-182.
43. P3/PC Diffractometer Program, Version 3.13; Bruker Analytical X-ray Instruments Inc.: Madison, WI; 1989.
44. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115-119.
45. Sheldrick, G. M. SHELXTL/IRIS; Bruker Analytical X-ray Instruments Inc.: Madison, WI, 1990.
46. Sheldrick, G. M. SHELXL-97; University of Göttingen: Gottingen Germany, 1997.
47. Supporting Information (atomic coordinates, anisotropic thermal parameters, bond distances and angles) has been deposited with the Cambridge Crystallographic Data Centre, with deposition numbers CCDC-137080 for 1a, CCDC-137077 for 1b, CCDC-137076 for 2a, and CCDC-137078 for 3a.
48. Stewart, R. F. Electrostatic properties of molecules from diffraction data. In The Application of Charge Density Research to Chemistry and Drug Design; Jeffrey, A., Piniella, J. F., Eds.; Plenum Press: New York, 1991; p 63 and references therein.
49. Stewart, R. F.; Spackman M. A., VALRAY users's manual; Department of Chemistry, Carnegie-Mellon University: Pittsburgh, 1983.
50. Clementi, E.; Roetti, C. At. Data Nucl. Data Tables 14 1974, 177-148.
51. van der Wal, R. J.; Stewart, R. F. Acta Crystallogr. 1984, A40, 587-593
52. Spackman, M. A. J. Chem. Phys. 1986, 85, 6579-6586.
53. Spackman, M. A.; Weber H. P.; Craven B. M. J. Am. Chem. Soc, 1988, 110, 775-782.
54. Saunders, V. R.; Dovesi, R.; Roetti, C.; Causà, M.; Harrison, N. M.; Orlando, R. Zicovich-Wilson C. M. CRYSTAL98, Version 1.0, User's Manual; 1999.
55. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
56. Hehre, W. J.; Radom, L.; Schleyer, P.v.R.; Pople, J. A. Ab initio molecular orbital theory, 1st ed.; John Wiley & Sons: New York, 1986; Chapter 4.
57. Ugliengo, P.; Viterbo, D.; Chiari, G. Z. Kristallogr. 1993, 207, 9-23. Available at http://www.ch.unito.it/ifm/fisica/moldraw/moldraw.html.