Tautomeric and conformational properties of acetoacetamide: Electron diffraction and quantum chemical study

Journal of Organic Chemistry

Volumn 71, Issue 14, 2006, Pages 5298-5302

  Belova, Natalya V ^a   Girichev, Georgiy V ^a   Shlykov, Sergey A ^a   Oberhammer, Heinz ^b  

^a IVANOVO STATE UNIVERSITY OF CHEMISTRY AND TECHNOLOGY   (Russian Federation)

^b UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOACETAMIDE; ENOL TAUTOMERS; GAS ELECTRON DIFFRACTION (GED); QUANTUM CHEMICAL CALCULATIONS;

ALCOHOLS; CHEMICAL BONDS; COMPOSITION; CONFORMATIONS; ELECTRON DIFFRACTION; ISOMERS;

NITROGEN COMPOUNDS;

ACETAMIDE DERIVATIVE; ACETOACETAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ELECTRON DIFFRACTION; ENERGY; GEOMETRY; QUANTUM CHEMISTRY; STRUCTURE ANALYSIS;

ACETOACETATES; AMIDES; ELECTRONS; GASES; HYDROGEN BONDING; MODELS, CHEMICAL; MOLECULAR CONFORMATION; QUANTUM THEORY;

EID: 33745685997     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060603e     Document Type: Article

References (25)

1. Emsley, J. Structure and Bonding; Springer: Berlin, 1984; Vol. 57, p 147.
2. Baughcum, S. L.; Duerst, R. W.; Rowe, W. F. J. Am. Chem. Soc. 1981, 103, 6296.
3. Baughcum, S. L.; Smith, Z.; Wilson, E. B.; Duerst, R. W. J. Am. Chem. Soc. 1984, 106, 2260.
4. Turner, P.; Baughcum, S. L.; Coy, S. L.; Smoth, Z. J. Am. Chem. Soc. 1984, 106 (8), 2265.
5. Lowrey, A. H.; George, C.; D'Antonio, P.; Karle, J. J. Am. Chem. Soc. 1971, 93 (24), 6399.
6. Andreassen, A. L.; Bauer, S. H. J. Mol. Struct. 1972, 12, 381.
7. Iijima, K.; Ohnogi, A.; Shibata, S. J. Mol. Struct. 1987, 156, 111.
8. Giricheva, N. I.; Girichev, G. V.; Lapshina, S. B.; Kuzmina, N. P. Zh. Strukt. Khim. 2000, 41 (1), 58 (in Russian).
9. Andreassen, A. L.; Zebelmann, D.; Bauer, S. H. J. Am. Chem. Soc. 1971, 93 (5), 1148.
10. Jin, A. D.; Mack, H.-G.; Waterfeld, A.; Oberhammer, H. J. Am. Chem. Soc. 1991, 113 (21), 7874.
11. Mack, H.-G.; Oberhammer, H.; Della Vedova, C. D. J. Mol. Struct. 1995, 346, 51.
12. Belova, N. V.; Oberhammer, H.; Girichev, G. V. J. Mol. Struct. 2004, 689, 255.
13. Kawashima, Y. 10th European Symposium on Gas Electron Diffraction, St. Petersburg, Russia, 2003.
14. sp corresponds to dihedral angles τ(O=C-C-C) of 0° ± 30°, sc to 60° ± 30°, ac to 120° ± 30°, and ap to 180° ± 30°.
15. Belova, N. V.; Oberhammer, H.; Girichev, G. V. J. Phys. Chem. A 2004, 108, 3593.
16. Bunting J. W., Kanter J. P. J. Am. Chem. Soc. 1993, 115, 11705.
17. Kontoyianni M., Bowen J. P. J. Comput. Chem. 1992, 13 (5), 657.
18. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb M. A.; Cheeseman, J. R.; Montgomery Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, 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.; Baboul, 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.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.04; Gaussian, Inc.: Pittsburgh, PA, 2003.
19. Sipachev, V. A. J. Mol. Struct. 2001, 567-568, 67.
20. Boyd R. J.; Boyd S. L. J. Am. Chem. Soc. 1992, 114, 1652.
21. Radeglia, R.; Scheithauer, S.; Mayer, R. Z. Naturforsch. 1969, 24b, 283.
22. Radeglia, R.; Scheithauer, S. Z. Chem. 1974, 14, 20.
23. Girichev, G. V.; Utkin, A. N.; Revichev, Yu. F. Prib. Tekh. Eksp. 1984, No. 2, 187 (in Russian).
24. Girichev, G. V.; Shlykov, S. A.; and Revichev, Yu. F. Prib. Tekh. Eksp. 1986, No. 4, 167 (in Russian).
25. Girichev, E. G.; Zakharov, A. V.; Girichev, G. V.; Bazanov M. I. Izv. Vyssh. Uchebn. Zaved., Technol. Text. Prom. 2000, 2, 142 (in Russian).