Quantification of the aromaticity of 2-alkylidenethiazolines subjected to push-pull activity

Journal of Organic Chemistry

Volumn 76, Issue 10, 2011, Pages 3861-3871

  Baranac Stojanović, Marija ^a,b,c   Kleinpeter, Erich ^c  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

^c UNIVERSITY OF POTSDAM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATICITIES; BOND ORBITALS; LONE PAIR; NUCLEUS-INDEPENDENT CHEMICAL SHIFTS;

CHEMICAL ANALYSIS; NUCLEAR MAGNETIC RESONANCE; SHIELDING;

CHEMICAL BONDS;

THIAZOLE DERIVATIVE;

AROMATICITY; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 79956151005     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200294f     Document Type: Article

References (87)

1. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317
2. Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Chem. Rev. 2005, 105, 3842
3. Schleyer, P. v. R.; Jiao, H.; Hommes, N. J. R. v. E.; Malkin, V. G.; Malkina, O. L. J. Am. Chem. Soc. 1997, 119, 12669
4. Schleyer, P. v. R.; Manoharan, M.; Wang, Z.-X.; Kiran, B.; Jiao, H.; Puchta, R.; Hommes, N. J. R. v. E. Org. Lett. 2001, 3, 2465
5. Fallah-Bagher-Shaidaei, H.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Org. Lett. 2006, 8, 863
6. Klod, S.; Kleinpeter, E. J. Chem. Soc., Perkin Trans. 2 2001, 1893
7. Ditchfield, R. Mol. Phys. 1974, 27, 789
8. Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1996, 104, 5497
9. SYBYL 7.1, Tripos Inc., St. Louis, MO, 2005.
10. Tóth, G.; Kovács, J.; Lévai, A.; Koch, A.; Kleinpeter, E. Magn. Reson. Chem. 2001, 39, 251
11. Kleinpeter, E.; Holzberger, A. Tetrahedron 2001, 57, 6941
12. Germer, A.; Klod, S.; Peter, M. G.; Kleinpeter, E. J. Mol. Model 2002, 8, 231
13. Kovács, J.; Tóth, G.; Simon, A.; Lévai, A.; Koch, A.; Kleinpeter, E. Magn. Reson. Chem. 2003, 41, 193
14. Szatmári, I.; Martinek, T. A.; Lázár, L.; Koch, A.; Kleinpeter, E.; Neuvonen, K.; Fülöp, F. J. Org. Chem. 2004, 69, 3645
15. Ryppa, C.; Senge, M. O.; Hatscher, S. S.; Kleinpeter, E.; Wacker, Ph.; Schilde, U.; Wiehe, A. Chem.-Eur. J 2005, 11, 3427
16. Kleinpeter, E.; Schulenburg, A.; Zug, I.; Hartmann, H. J. Org. Chem. 2005, 70, 6592
17. Kleinpeter, E.; Schulenburg, A. J. Org. Chem. 2006, 71, 3869
18. Heydenreich, M.; Koch, A.; Klod, S.; Szatmári, I.; Fülöp, F.; Kleinpeter, E. Tetrahedron 2006, 62, 11081
19. Kleinpeter, E.; Koch, A.; Sahoo, H. S.; Chand, D. K. Tetrahedron 2008, 64, 5044
20. Kleinpeter, E.; Koch, A.; Seidl, P. R. J. Phys. Chem. A 2008, 112, 4989
21. Kleinpeter, E.; Szatmári, I.; Lázár, L.; Koch, A.; Heydenreich, M.; Fülöp, F. Tetrahedron 2009, 65, 8021
22. Kleinpeter, E.; Klod, S.; Koch, A. THEOCHEM 2007, 811, 45 and references therein Kleinpeter, E.; Klod, S.; Koch, A. THEOCHEM 2008, 857, 89
23. Kleinpeter, E.; Koch, A.; Shainyan, B. A. THEOCHEM 2008, 863, 127
24. Kleinpeter, E.; Klod, S.; Koch, A. J. Org. Chem. 2008, 73, 1498
25. Kleinpeter, E.; Koch, A. THEOCHEM 2010, 939, 1
26. Kleinpeter, E.; Koch, A. THEOCHEM 2008, 851, 313
27. Kleinpeter, E.; Klod, S. J. Am. Chem. Soc. 2004, 126, 2231
28. Klod, S.; Koch, A.; Kleinpeter, E. J. Chem. Soc., Perkin Trans. 2 2002, 1506
29. Kleinpeter, E.; Koch, A. J. Phys. Chem. A 2010, 114, 5928
30. Sandström, J. Top. Stereochem. 1983, 14, 83
31. Fischer, G.; Rudorf, W.-D.; Kleinpeter, E. Magn. Reson. Chem. 1991, 29, 212
32. Benassi, R.; Bertarini, C.; Kleinpeter, E.; Taddei, F. THEOCHEM 2000, 498, 217
33. Kleinpeter, E.; Klod, S.; Rudorf, W.-D. J. Org. Chem. 2004, 69, 4317
34. Rattananakin, P.; Pittman, C. R., Jr.; Collier, W. E.; Saebø, S. Struct. Chem. 2007, 18, 399
35. Ye, G.; Chatterjee, S.; Li, M.; Zhou, A.; Song, Y.; Barker, B. L.; Chen, C.; Beard, D. J.; Henry, W. P.; Pittman, C. U. Tetrahedron 2010, 66, 2919 and references therein
36. Kleinpeter, E; Thomas, St.; Uhlig, G.; Rudorf, W.-D. Magn. Reson. Chem. 1993, 31, 714
37. Kleinpeter, E; Heydenreich, M.; Chatterjee, S. K.; Rudorf, W.-D. Magn. Reson. Chem. 1994, 32, 473
38. Kleinpeter, E; Koch, A.; Heydenreich, M.; Chatterjee, S. K.; Rudorf, W.-D. J. Mol. Struct. 1995, 356, 25
39. Mueller, J. L.; Gibson, M. S.; Hartman, J. S. Can. J. Chem. 1996, 74, 1329
40. Chiara, J. L.; Gómez-Sánchez, A.; Bellanato, J. J. Chem. Soc., Perkin Trans. 2 1998, 1797
41. Kleinpeter, E.; Heydenreich, M.; Woller, J.; Wolf, G; Koch, A.; Kempter, G. J. Chem. Soc., Perkin Trans. 2 1998, 1877
42. Meier, H.; Mühling, B.; Gerold, J.; Jacob, D.; Oehlhof, A. Eur. J. Org. Chem. 2007, 625
43. Kleinpeter, E. J. Serb. Chem. Soc. 2006, 71, 1
44. Kleinpeter, E.; Schulenburg, A. Tetrahedron Lett. 2005, 46, 5995
45. Baranac-Stojanović, M.; Klaumünzer, U.; Marković, R.; Kleinpeter, E. Tetrahedron 2010, 66, 8958
46. Kleinpeter, E.; Schulenburg, A.; Zug, I.; Hartmann, H. J. Org. Chem. 2005, 70, 6592
47. Kleinpeter, E.; Frank, A. J. Phys. Chem. A 2009, 113, 6774
48. Kleinpeter, E.; Frank, A. Tetrahedron 2009, 65, 4418
49. Kleinpeter, E.; Schulenburg, A. J. Org. Chem. 2006, 71, 3869
50. Kleinpeter, E.; Stamboliyska, B. A. Tetrahedron 2009, 65, 9211
51. Kleinpeter, E.; Bölke, U.; Kreicberga, J. Tetrahedron 2010, 66, 4503
52. Kleinpeter, E.; Stamboliyska, B. A. J. Org. Chem. 2008, 73, 8250
53. Bohmann, J. A.; Weinhold, F.; Farrar, T. C. J. Chem. Phys. 1997, 107, 1173
54. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennuci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Babuol, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzales, C.; Pople, J. A. Gaussian 03(Revision C.02); Gaussian, Inc., Wallingford, CT, 2004.
55. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618
56. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
57. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, 37, 785 This was the highest possible level for computation of ICSS. The lattice points ("ghost atoms") should be sensor points only without energy contribution in the present calculations. Only if HF calculations were applied did this prove to be true; in the case of electron correlation calculations, the "ghost atoms" get their own electron density and are of some influence on the energy of the studied molecule hereby. In these cases, the TSNMRS surfaces proved to become heavily distorted.
58. Bohmann, J. A.; Weinhold, F.; Farrar, T. C. J. Chem. Phys. 1997, 107, 1173
59. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheesman, 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.; Rega, N.; Salvador, P.; Dannenberg, J. J.; 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.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzales, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11.3; Gaussian Inc.; Pittsburgh, PA, 2002.
60. González, F. V.; Jain, A.; Rodríguez, S.; Sáez, J. A.; Vicent, C.; Teris, G. J. Org. Chem. 2010, 75, 5888
61. Raşović, A.; Steel, P. J.; Kleinpeter, E.; Marković, R. Tetrahedron 2006, 63, 1937 and references cited therein
62. Andreu, R.; Cerdán, M. A.; Garín, H.; Orduna, J. Arkivoc 2004, iv, 32
63. Fragoso-Serrano, M.; Guillén-Jaramillo, G.; Pereda-Miranda, R.; Cerda-García-Rojas, C. M. J. Org. Chem. 2003, 68, 7167
64. Iwaoka, M.; Takemoto, S.; Tomoda, S. J. Am. Chem. Soc. 2002, 124, 10613
65. Dal Colle, M.; Bertolasi, V.; de Palo, M.; Distefano, G.; Jones, D.; Modelli, A.; Olivato, P. R. J. Phys. Chem. 1995, 99, 15011
66. Burling, F. T.; Goldstein, B. M. J. Am. Chem. Soc. 1992, 114, 2313
67. Fabius, B.; Cohen-Addad, C.; Larsen, F. K.; Lehmann, M. S.; Becker, P. J. Am. Chem. Soc. 1989, 111, 5728
68. Hordvik, A.; Jynge, K. Tetrahedron 1979, 35, 1199
69. Rosenfield, R. E., Jr.; Parthasarathy, R.; Dunitz, J. D. J. Am. Chem. Soc. 1977, 99, 4860
70. Mellor, I. P.; Nyburg, S. C. Acta Crystallogr. 1971, B27, 1959
71. Geometry optimization of the s-trans/s-trans conformation of 1r actually gave the s-cis/s-trans conformation II.
72. Twist angle is defined as the angle between the bisectors of the 1,1- and 2,2-substituent angles on a Newman diagram projecting down the C - C bond of an olefin. See: Baum, K; Bigelow, S. S.; Nguyen, N. V.; Archibald, T. G. J. Org. Chem. 1992, 57, 235
73. Winkler, F. K.; Dunitz, J. D. J. Mol. Biol. 1971, 59, 169
74. Kleinpeter, E.; Bölke, U.; Koch, A. J. Phys. Chem. A 2010, 114, 7616
75. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 4907
76. In some compounds, there is still a small contribution of substituents anisotropic effects to the ICSS = 0.5 ppm, so that the values are somewhat higher.
77. Wiberg, K. B. Tetrahedron 1968, 24, 1083
78. Krygowski, T. M.; Cyra?ski, M. K. Chem. Rev. 2001, 101, 1385
79. Krygowski, T. M.; Cyra?ski, M. K. Tetrahedron 1996, 52, 10255
80. Krygowski, T. M.; Cyra?ski, M. K. Tetrahedron 1996, 52, 1713
81. Kruszewski, J.; Krygowski, T. M. Tetrahedron Lett. 1972, 3839
82. Cyra?ski, M. K.; Krygowski, T. M.; Katritzky, A. R.; Schleyer, P. v. R. J. Org. Chem. 2002, 67, 1333
83. Pople, J. A. J. Chem. Phys. 1956, 24, 1111
84. Wannere, C. S.; Schleyer, P. v. R. Org. Lett. 2003, 5, 605
85. Viglione, R. G.; Zanasi, R.; Lazzeretti, P. Org. Lett. 2004, 6, 2265
86. Wannere, C. S.; Corminboeuf, C.; Allen, W. D.; Schaefer, H. F.; Schleyer, P.; von, R. Org. Lett. 2005, 7, 1457
87. The total contributions of the ring C-H bonds, N-H(Me, t -Bu), and C(2) - C(2′) bond are much smaller, especially to the out-of-plane magnetic shielding.