Theoretical investigations on the structure of poly(iminomethylenes) with alipathic side chains. Conformational studies and comparison with experimental spectroscopic data

Journal of the American Chemical Society

Volumn 119, Issue 5, 1997, Pages 1059-1071

  Clericuzio, M ^a,b   Alagona, G ^c   Ghio, C ^c   Salvadori, P ^d  

^a SCUOLA NORMALE SUPERIORE   (Italy)

^b CHEMICAL CENTER   (Sweden)

^c CNR   (Italy)

^d UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

POLYETHYLENE DERIVATIVE; POLYMER;

ARTICLE; CIRCULAR DICHROISM; DRUG STRUCTURE; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; SPECTROPHOTOMETRY; THEORY;

EID: 0031019184     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961692n     Document Type: Article

References (74)

1. Yamamoto, Y.; Takizawa, T.; Hagihara, N. Nippon Kagaku Zasshi 1966, 87, 1355.
2. Saegusa, T.; Taka-Ishi, N.; Ito, Y. J. Org. Chem. 1969, 34, 4040.
3. Millich, F.; Sinclair, R. G., II J. Polym. Sci., A-1 1968, 6, 1417. Ibid. Part C 13, 2150. J. Polym. Sci., C 1968, 22, 33.
4. Millich, F.; Sinclair, R. G., II J. Polym. Sci., A-1 1968, 6, 1417. Ibid. Part C 13, 2150. J. Polym. Sci., C 1968, 22, 33.
5. Millich, F.; Sinclair, R. G., II J. Polym. Sci., A-1 1968, 6, 1417. Ibid. Part C 13, 2150. J. Polym. Sci., C 1968, 22, 33.
6. Nolte, R. J. M.; Stephany, R. W.; Drenth, W. Recl. Trav. Chim. Pays-Bas 1973, 92, 83. Nolte, R. J. M.; Drenth, W. Recl. Trav. Chim. Pays-Bas 1973, 92, 788.
7. Nolte, R. J. M.; Stephany, R. W.; Drenth, W. Recl. Trav. Chim. Pays-Bas 1973, 92, 83. Nolte, R. J. M.; Drenth, W. Recl. Trav. Chim. Pays-Bas 1973, 92, 788.
8. Nolte, R. J. M.; Zwikker, J. W.; Reedijk, J.; Drenth, W. J. Mol. Catal. 1978, 4, 423. Van Beijnen, A. J. M.; Nolte, R. J. M.; Zwikker, J. W.; Drenth, W. J. Mol. Catal. 1978, 4, 427.
9. Nolte, R. J. M.; Zwikker, J. W.; Reedijk, J.; Drenth, W. J. Mol. Catal. 1978, 4, 423. Van Beijnen, A. J. M.; Nolte, R. J. M.; Zwikker, J. W.; Drenth, W. J. Mol. Catal. 1978, 4, 427.
10. Millich, F. Chem. Rev. 1972, 72, 101.
11. Millich, F. Adv. Polym. Sci. 1975, 19, 117.
12. Millich, F. Macromol. Rev. 1980, 15, 207.
13. Drenth, W.; Nolte, R. J. M. Acc. Chem. Res. 1979, 12, 30.
14. Teerenstra, M. N.; Hagting, J. G.; Oostergetel, G. T.; Scheuten, A. J.; Devillers, M. A. C.; Nolte, R. J. M. Thin Solid Films 1994, 248, 110.
15. Kauranen, M.; Verbiest, T.; Meijer, E. W.; Havinga, E. E.; Teerenstra, M. N.; Schouten, A. J.; Nolte, R. J. M.; Persoons, A. Adv. Mater. 1995, 7, 641. Kauranen, M.; Verbiest, T.; Boutton, C.; Teerenstra, M. N.; Clays, K.; Schouten, A. J.; Nolte, R. J. M.; Persoons, A. Science 1995, 270, 966.
16. Kauranen, M.; Verbiest, T.; Meijer, E. W.; Havinga, E. E.; Teerenstra, M. N.; Schouten, A. J.; Nolte, R. J. M.; Persoons, A. Adv. Mater. 1995, 7, 641. Kauranen, M.; Verbiest, T.; Boutton, C.; Teerenstra, M. N.; Clays, K.; Schouten, A. J.; Nolte, R. J. M.; Persoons, A. Science 1995, 270, 966.
17. Yamagishi, A.; Tanaka, I.; Taniguchi, M.; Takahashi, M. J. Chem. Soc., Chem. Commun. 1994, 1113.
18. Millich, F.; Sinclair, R. G., II. Polym. Prepr. 1965, 6, 736.
19. Millich, F.; Baker, G. K. Macromolecules 1969, 2, 122.
20. Huang, S. Y.; Hellmuth, E. W. Polym. Prepr. 1974, 15, 499.
21. Van Beijnen, A. J. M.; Nolte, R. J. M.; Naaktgeboren, A. J.; Zwikker, J. W.; Drenth, W.; Hezemans, A. M. F. Macromolecules 1983, 16, 1679.
22. Harada, T.; Cleij, M. C.; Nolte, R. J. M.; Hezemans, A. M. F.; Drenth, W. J. Chem. Soc., Chem. Commun. 1984, 726.
23. King, R. B.; Greene, M. J. J. Polym. Sci. (Polym. Chem.) 1987, 25, 907.
24. Green, M. M.; Gross, R. A.; Schilling, F.; Zero, K.; Crosby, C., III. Macromolecules 1988, 21, 1839.
25. Pini, D.; Iuliano, A.; Salvadori, P. Macromolecules 1992, 25, 6059.
26. Huige, C. J. M. Determination of the conformations of some poly(iminomethylenes) by means of Molecular Mechanics and Circular Dichroism; Ph.D. thesis, University of Utrecht, The Netherlands, 1985.
27. Huige, C. J. M.; Spek, A. L.; De Boer, J. L. Acta Crystallogr. 1985, C41, 113.
28. Melberg, S.; Rasmussen, K. J. Mol. Struct. 1979, 57, 215.
29. Kollmar, C.; Hoffmann, R. J. Am. Chem. Soc. 1990, 112, 8230.
30. Gaussian 92/DFT, Revision G.2, Frish, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Wong, M. W.; Foresman, J. B.; Robb, M. A.; Head-Gordon, M.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzales, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A.; Gaussian Inc., Pittsburgh, PA, 1993.
31. MM3(89), Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551. Lii, J.-H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8566. Lii, J.-H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8576.
32. MM3(89), Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551. Lii, J.-H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8566. Lii, J.-H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8576.
33. MM3(89), Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551. Lii, J.-H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8566. Lii, J.-H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8576.
34. PCMODEL (Version 2.0), program of Gilbert, K. E., Gajewski, J. J., available from Serena Software, Bloomington, IN.
35. Meier, J.; Bauder, A.; Gunthard, Hs. H. J. Chem. Phys. 1972, 57, 1219.
36. De Voe, H. J. Chem. Phys. 1964, 41, 393. Ibid. 1965, 43, 3199.
37. De Voe, H. J. Chem. Phys. 1964, 41, 393. Ibid. 1965, 43, 3199.
38. Hug, W.; Ciardelli, F.; Tinoco, I., Jr. J. Am. Chem. Soc. 1974, 96, 3407.
39. Rosini, C.; Zandomeneghi, M.; Salvadori, P. Tetrahedron Asymm. 1993, 4, 545.
40. Tinoco, I., Jr. Adv. Chem. Phys. 1962, 4, 113.
41. Schellman, J. A.; Nielsen, E. B. J. Phys. Chem. 1967, 71, 3914.
42. Texter, J.; Stevens, E. S. J. Chem. Phys. 1978, 69, 1680.
43. Benedix, R.; Birner, P.; Birnstock, F.; Hennig, H.; Hofmann, H. J. J. Mol. Struct. 1979, 51, 99. The authors apply an NDDO semiempirical MO-SCF method to (E,E)-ethanediimine and demonstrate that inclusion of the directed interaction of N lone pairs is essential to have a correct cis/trans energy separation.
44. Hargittai, I.; Seip, R. Acta Chem. Scand. 1976, A30, 540.
45. Exner, O.; Kliegman, J. M. J. Org. Chem. 1971, 36, 2015.
46. Strictly speaking, the terms isotactic and syndiotactic could not be employed in this case, as they refer to the stereochemistry of (pseudo)-asymmetric carbon atoms. We use them as labels to facilitate comprehension of the physical situation.
47. Kamer, P. C. J.; Drenth, W.; Nolte, R. J. M. Polym. Prepr. (ACS Div. Polym. Chem.) 1989, 30, 418.
48. Sastry, K. V. L. N.; Curl, R. F., Jr. J. Chem. Phys. 1964, 41, 77. Yardley, J. T.; Hinze, J.; Curl, R. F., Jr. J. Chem. Phys. 1964, 41, 2562.
49. Sastry, K. V. L. N.; Curl, R. F., Jr. J. Chem. Phys. 1964, 41, 77. Yardley, J. T.; Hinze, J.; Curl, R. F., Jr. J. Chem. Phys. 1964, 41, 2562.
50. Nolte, R. J. M.; van Beijnen, A. J. M.; Drenth, W. J. Am. Chem. Soc. 1974, 96, 5932. HPLC = high pressure liquid chromatography.
51. Van Beijnen, A. J. M.; Nolte, R. J. M.; Drenth, W.; Hezemans, A. M. F. Tetrahedron 1976, 32, 2017.
52. Van Beijnen, A. J. M.; Nolte, R. J. M.; Naaktgeboren, A. J.; Zwikker, J. W.; Drenth, W.; Hezemans, A. M. F. Macromolecules 1983, 16, 1679.
53. Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 4400.
54. Pino, P.; Luisi, P. L. J. Chim. Phys. 1968, 65, 130.
55. Lifson, S.; Andreola, C.; Peterson, N. C.; Green, M. M. J. Am. Chem. Soc. 1989, 111, 8850.
56. Program based on a least-square algorithm, written by Pelliccioni, A. (CNR, Rome, Italy).
57. Bonnett, R. In Chemistry of the Carbon-Nitrogen Double Bond; Patai, S., Ed.; Interscience: New York, 1970.
58. Smith, H. E.; Chen, F. M. J. Org. Chem. 1979, 44, 2775.
59. Nandi, S. D. Tetrahedron 1972, 28, 845.
60. CNDO/S, Del Bene, J.; Jaffé, H. H. J. Chem. Phys. 1968, 48, 1807. Ibid. 1968, 49, 1221. Ibid. 1969, 50, 1126. Ellis, R. L.; Kuehnlenz, G.; Jaffé, H. H. Theor. Chim. Acta 1972, 26, 131.
61. CNDO/S, Del Bene, J.; Jaffé, H. H. J. Chem. Phys. 1968, 48, 1807. Ibid. 1968, 49, 1221. Ibid. 1969, 50, 1126. Ellis, R. L.; Kuehnlenz, G.; Jaffé, H. H. Theor. Chim. Acta 1972, 26, 131.
62. CNDO/S, Del Bene, J.; Jaffé, H. H. J. Chem. Phys. 1968, 48, 1807. Ibid. 1968, 49, 1221. Ibid. 1969, 50, 1126. Ellis, R. L.; Kuehnlenz, G.; Jaffé, H. H. Theor. Chim. Acta 1972, 26, 131.
63. CNDO/S, Del Bene, J.; Jaffé, H. H. J. Chem. Phys. 1968, 48, 1807. Ibid. 1968, 49, 1221. Ibid. 1969, 50, 1126. Ellis, R. L.; Kuehnlenz, G.; Jaffé, H. H. Theor. Chim. Acta 1972, 26, 131.
64. The use of configuration interaction in CNDO/S calculations has been subjected to criticisms: see, for instance, Bouman, T. D.; Lightner, D. A. J. Am. Chem. Soc. 1976, 98, 3145. The authors find that inclusion of CI shifts the n-π* transition of ketones at too low energies, exactly what was found by us in our diimine.
65. Tinoco, I., Jr. J. Chim. Phys. 1968, 65, 91.
66. Snyder, P. A.; Johnson, W. C., Jr. J. Chem. Phys. 1973, 59, 2618. Snyder, P. A.; Johnson, W. C., Jr. J. Am. Chem. Soc. 1978, 100, 2939.
67. Snyder, P. A.; Johnson, W. C., Jr. J. Chem. Phys. 1973, 59, 2618. Snyder, P. A.; Johnson, W. C., Jr. J. Am. Chem. Soc. 1978, 100, 2939.
68. Clericuzio, M. Ph.D. thesis, Scuola Normale Superiore, Pisa, 1993.
69. Höhn, E. G.; Weigang, O. E., Jr. J. Chem. Phys. 1968, 48, 1127.
70. Snyder, P. A.; Johnson, W. C., Jr. Biopolymers 1973, 12, 975.
71. Woody, R. W.; Tinoco, I., Jr. J. Chem. Phys. 1967, 46, 4927.
72. In De Voe calculations only the transitions of the iminic chromophore were taken into account. In dynamic ones the contribution of side chains (C-C and C-H bonds) were considered, too. However, in the present case the optical activity due to side chains is small compared to that of the iminic backbone.
73. An analogous calculation using the dynamic method would be complicated by (i) the predicted presence of two "n-π*" transitions; (ii) the nonobvious localization of the transitions themselves and of the relative quadrupolar transition charges.
74. Bystricky, S.; Koos, M.; Repas, M. Chem. Zvest. 1981, 35, 679.