Comment on "single-crystal x-ray structure of 1,3- dimethylcyclobutadiene by confinement in a crystalline matrix"

Science

Volumn 330, Issue 6007, 2010, Pages

  Alabugin, Igor V ^a   Gold, Brian ^a   Shatruk, Michael ^a   Kovnir, Kirill ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIMETHYLCYCLOBUTADIENE; ALKENE DERIVATIVE; CARBON DIOXIDE; LACTONE; UNCLASSIFIED DRUG;

ACCURACY; CALCULATION; CHEMICAL PARAMETERS; CHEMICAL STRUCTURE; COVALENT BOND; CRYSTAL STRUCTURE; DENSITY; ENERGY; GEOMETRY; NOTE; PREDICTION; PRIORITY JOURNAL; THERMODYNAMICS; X RAY;

EID: 78449309746     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1196188     Document Type: Note

References (20)

1. J. L. Menke, E. V. Patterson, R. J. McMahon, J. Phys. Chem. A 114, 6431 (2010).
2. A. Balková, R. J. Bartlett, J. Chem. Phys. 101, 8972 (1994).
3. W. T. Borden, E. R. Davidson, P. Hart, J. Am. Chem. Soc. 100, 388 (1978).
4. L. Watts, J. D. Fitzpatrick, R. Pettit, J. Am. Chem. Soc. 87, 3253 (1965).
5. G. Maier, Angew. Chem. Int. Ed. Engl. 13, 425 (1974).
6. T. Bally, S. Masamune, Tetrahedron 36, 343 (1980).
7. B. R. Arnold, J. Michl, in Kinetics and Spectroscopy of Carbenes and Biradicals, M. S. Platz, Ed. (Plenum, New York, 1990), chap. 1.
8. D. W. Whitman, B. K. Carpenter, J. Am. Chem. Soc. 102, 4272 (1980).
9. E. J. Corey, J. Streith, J. Am. Chem. Soc. 86, 950 (1964).
10. M. Rosenblum, B. North, J. Am. Chem. Soc. 90, 1060 (1968).
11. C. Y. Lin, A. Krantz, J. Chem. Soc. Chem. Comm. 1972, 1111 (1972).
12. Y.-M. Legrand, A. van der Lee, M. Barboiu, Science 329, 299 (2010).
13. D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. Int. Ed. Engl. 30, 1024 (1991).
14. F. Toda, Eur. J. Org. Chem. 2000, 1377 (2000).
15. In the actual crystallographic information file provided as supporting information by Legrand et al. (12), this bond is even longer, 1.79(3) Å. Thus, there is also an obvious discrepancy between the values given in the text and those found in the crystal structure of the purported Dewar intermediate.
16. DFT calculations were performed at the B3LYP/6-31G** level of theory.
17. R. S. Rowland, R. Taylor, J. Phys. Chem. 100, 7384 (1996).
18. O. L. Chapman, C. L. McIntosh, J. Pacansky, J. Am. Chem. Soc. 95, 614 (1973).
19. R. G. S. Pong, B.-S. Huang, J. Laureni, A. Krantz, J. Am. Chem. Soc. 99, 4153 (1977).
20. I.V.A. is funded in part by the National Science Foundation (CHE-0848686) and Petroleum Research Fund, administered by the American Chemical Society (Award 47590-AC4).