Highly twisted C=C double bonds in 4-methyleneisoxazolones

Australian Journal of Chemistry

Volumn 62, Issue 9, 2009, Pages 1068-1078

  Kvaskoff, David ^a   Bernhardt, Paul V ^a   Koch, Rainer ^b   Wentrup, Curt ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COALESCENCE; DENSITY FUNCTIONAL THEORY;

B3LYP/6-31G; C-C DOUBLE BONDS; CHARGE SEPARATIONS; CRYSTALLOGRAPHIC DATA; DENSITY FUNCTIONAL THEORY CALCULATIONS; DIHEDRAL ANGLES; DOUBLE BONDS; GOOD CORRELATIONS; NEGATIVE CHARGE; ORBITAL OCCUPATION; ROTATIONAL BARRIERS; SINGLE BOND; TWISTING ANGLE; ZWITTERIONIC STRUCTURE;

X RAY CRYSTALLOGRAPHY;

EID: 84962439407     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH09359     Document Type: Conference Paper

References (47)

1. (a) J. Sandström, Top. Stereochem. 1983, 14, 84.
2. (b) J. Sandström, in The Chemistry of Enamines (Ed. Z. Rappoport) 1994, Ch. 6, pp. 405-436 (Wiley: Chichester
3. (c) M. W. Wong, M. J. Frisch, K. B. Wiberg, J. Am. Chem. Soc. 1991, 113, 4776. doi:10.1021/JA00013A010
4. (d) R. R. Pappalardo, E. S. Marcos, M. F. Ruiz-Lopez, D. Rinaldi, J. L. Rivail, J.Am. Chem. Soc. 1993, 115, 3722. doi:10.1021/JA00062A043
5. For an educational paper on "Rotational Barriers in Push-Pull Ethylenes; an Advanced Physical-Organic Project Including 2D EXSY and Computational Chemistry", see T. J. Dwyer, J. E. Norman, P. G. Jasien, J. Chem. Educ. 1998, 75, 1635.
6. A. J. Kay, A. D. Woolhouse, G. J. Gainsford, T. G. Haskell, C. P. Wyss, S. M. Giffin, I. T. McKinnie, T. H. Barnes, J. Mater. Chem. 2001, 11, 2271. doi:10.1039/B103148C
7. P. V. Bernhardt, R. Koch, D. W. Moloney, M. Shtaiwi, C. Wentrup, J. Chem. Soc., Perkin Trans. 2 2002, 515. doi:10.1039/B109624A
8. R. N. Veedu, P. V. Bernhardt, R. Koch, C. Wentrup, Aust. J. Chem. 2008, 61, 805. doi:10.1071/CH08277
9. S.Abrahamsson, G. Rehnberg,T. Liljefors,Acta Chem. Scand. B 1974, 28b, 1109. doi:10.3891/ACTA.CHEM.SCAND.28B-1109
10. (a) R. Destro, U. Consentino, G. Moro, E. Ortoleva, T. Pilati, J. Mol. Struct. 1989, 212, 97. doi:10.1016/0022-2860(89)85070-7
11. (b) A. Forni, R. Destro, Chem. Eur. J. 2003, 9, 5528. doi:10.1002/ CHEM.200305043
12. K. Baum, S. S. Bigelow, N. V. Nguyen, T. G. Archibald, J. Org. Chem. 1992, 57, 235. doi:10.1021/JO00027A042
13. (a) D. Adhikesavalu, K. Venkatesan, Acta Crystallogr. C 1983, 39, 1044. doi:10.1107/S0108270183007313
14. (b) D. Adhikesavalu, K. Venkatesan, Acta Crystallogr. C 1983, 39, 1424. doi:10.1107/S0108270183008744
15. (c)D. Kanagapushpam, K. Venkatesan, T. S. Cameron, Acta Crystal-logr. C 1988, 44, 337. doi:10.1107/S0108270187009776
16. (d) A. J. Blake, H. McNab, L. C. Monahan, J. Chem. Soc., Perkin Trans. 1991, 2, 2003.
17. (e) A. J. Blake, H. McNab, K. Withell, Acta Crystallogr. Sect. E Struct. Rep. Online 2003, 59, o841. doi:10.1107/S1600536803010432 (Pubitemid 40651230)
18. (f)R. O. Gould, S. G. Harris, H. McNab, S. Parsons, K. Withell, Acta Crystallogr. C 1998, 54, 234. doi:10.1107/S0108270197014170
19. (g)J. K. Mukhopadhyaya, S. Sklenak, Z. Rappoport, J. Am. Chem. Soc. 2000, 122, 1325. doi:10.1021/JA992059F (Pubitemid 30120415)
20. I. Alkorta, C. Wentrup, J. Elguero, J. Mol. Struct. Theochem. 2002, 585, 27. doi:10.1016/S0166-1280(02)00036-2
21. (a) E. Kleinpeter, S. Klod, W.-D. Rudorf, J. Org. Chem. 2004, 69, 4317. doi:10.1021/JO0496345 (Pubitemid 38856219)
22. (b) E. Kleinpeter, A. Schulenburg, Tetrahedron Lett. 2005, 46, 5995. doi:10.1016/J.TETLET.2005.07.030 (Pubitemid 41096568)
23. (a)E. Kleinpeter, A. Frank, Tetrahedron 2009, 65, 3318.
24. (b)E. Kleinpeter, A. Frank, J. Phys. Chem. A 2009, 113, 6774. doi:10.1021/JP9024359
25. (a)R. Flammang, D. Landu, S. Laurent, M. Barbieux-Flammang, C. O. Kappe, M. W. Wong, C. Wentrup, J. Am. Chem. Soc. 1994, 116, 2005. doi:10.1021/ JA00084A046
26. G. I. Yranzo, J. Elguero, R. Flammang, C. Wentrup, Eur. J. Org. Chem. 2001, 2209. doi:10.1002/1099-0690(200106)2001:12<2209:: AID-EJOC2209>3.0. CO;2-X
27. R. Wolf, S. Stadtmüller, M. W. Wong, M. Barbieux-Flammang, R. Flammang, C. Wentrup, Chem. Eur. J. 1996, 2, 1318. doi:10.1002/ CHEM.19960021020
28. C. O. Kappe, D. Kvaskoff, D. W. J. Moloney, R. Flammang, C. Wentrup, J. Org. Chem. 2001, 66, 1827. doi:10.1021/JO001595J (Pubitemid 32205123)
29. H.-J. Wollweber, C. Wentrup, J. Org. Chem. 1985, 50, 2041. doi:10.1021/JO00212A007
30. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. J. A. Montgomery, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox,T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03 2004 (Gaussian, Inc.: Pittsburgh, PA
31. (a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648. doi:10.1063/1.464913
32. (b)C. Lee, W. Yang, R. G. Parr, Phys. Rev. B Condens. Matter 1988, 37 , 785. doi:10.1103/PHYSREVB.37.785
33. (a)P. C. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213. doi:10.1007/BF00533485
34. (b)W. J. Pietro, M. M. Francl, W. J. Hehre, D. J. DeFrees, J. A. Pople, J. S. Binkley, J. Am. Chem. Soc. 1982, 104, 5039. doi:10.1021/ JA00383A007
35. (a)S. Mierts, E. Scrocco, J. Tomasi, Chem. Phys. 1981, 55, 117. doi:10.1016/0301-0104(81)85090-2
36. (b)S. Mierts, J.Tomasi, Chem. Phys. 1982, 65, 239. doi:10.1016/0301- 0104(82)85072-6
37. (c)M. Cossi, V. Barone, R. Cammi, J. Tomasi, Chem. Phys. Lett. 1996, 255, 327. doi:10.1016/0009-2614(96)00349-1
38. (d)E. Cances, B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 107, 3032. doi:10.1063/1.474659
39. (e) M. Cossi, V. Barone, B. Mennucci, J. Tomasi, Chem. Phys. Lett. 1998, 286, 253. doi:10.1016/S0009-2614(98)00106-7
40. E. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C. M. Morales, F. Weinhold, 2004 (Theoretical Chemistry Institute, University of Wisconsin, Madison, WI); http://www.chem.wisc.edu/~nbo5 (accessed 17 November 2008
41. (a) A. Hantzsch, Ber. Dtsch. Chem. Ges. 1891, 24, 495. doi:10.1002/CBER.18910240193
42. A. R. Katritzky, S. Øksne, A. J. Boulton, Tetrahedron 1962, 18, 777. doi:10.1016/S0040-4020(01)92728-0
43. M. W. Rathke, J. Am. Chem. Soc. 1970, 92, 3222. doi:10.1021/ JA00713A071
44. L. J. Farrugia, J. Appl. Cryst. 1999, 32, 837. doi:10.1107/ S0021889899006020
45. G. M. Sheldrick, SHELX97, Programs for Crystal Structure Analysis (Release 97-2) 1998 (Institüt für Anorganische Chemie der Universität: Göttingen, Germany
46. L. J. Farrugia, J. Appl. Cryst. 1997, 30, 565. doi:10.1107/ S0021889897003117
47. A. L. Spek, PLATON, A Multipurpose Crystallographic Tool 1998 (Utrecht University: Utrecht, The Netherlands