Sluggish σ-bond formation between sp-hybridized carbons: Acetylide coupling on Ag(111)

Journal of the American Chemical Society

Volumn 129, Issue 5, 2007, Pages 1028-1029

  Kung, Hsuan ^a   Lee, Long Cheng ^a   Wu, Shin Mou ^a   Cheng, Hsiu Yao ^b   Chiang, Chao Ming ^a  

^a NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

^b TUNGHAI UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CARBON; SILVER;

ARTICLE; CHEMICAL BOND; CROSS COUPLING REACTION; DEHYDROGENATION; DESORPTION; DIFFUSION; DIMERIZATION; ENERGY; HYBRIDIZATION; INFRARED SPECTROSCOPY; MOLECULAR INTERACTION; SURFACE PROPERTY; TEMPERATURE DEPENDENCE;

ACETYLENE; CARBON; CATALYSIS; ORGANOMETALLIC COMPOUNDS; SILVER; SPECTROPHOTOMETRY, INFRARED; TEMPERATURE;

EID: 33846807574     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066066x     Document Type: Article

References (17)

1. Marsden, J. A.; Haley, M. M. Cross-Coupling Reactions to sp Carbon Atoms. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 317-394.
2. Ma, Z.; Zaera, F. Surf. Sci. Rep. 2006, 61, 229-281.
3. Zhou, X.-L.; White, J. M. J. Phys. Chem. 1991, 95, 5575-5580.
4. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principle and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; pp 322-333.
5. Zaera, F. Chem. Rev. 1995, 95, 2651-2693.
6. Barteau, M. A.; Madix, R. J. Surf. Sci. 1982, 115, 355-381.
7. Vohs, J. M.; Carney, D. A.; Barteau, M. A. J. Am. Chem. Soc. 1985, 107, 7841-7848.
8. Nyquist, R. A. Spertrochim. Acta 1965, 21, 1245-1255.
9. Fan, J.; Trenary, M. Lanymuir 1994, 10, 3649-3657.
10. 7 hexagonal cluster, where the acetylide group is bound to the center Ag atom. Adding an adjacent fixed iodine atom and an extra negative charge (making charge = -1 and multiplicity = 1) renders the most fitted IR spectrum.
11. NIST Computational Chemistry Comparison and Benchmark DataBase, http://srdata.nist.gov/cccbdb/vsf.asp.
12. 6 coupling product yield (shown in the inset of Figure 2a).
13. Zhou, X.-L.; Schwaner, A. L.; White, J. M. J. Am. Chem. Soc. 1993, 115, 4309-4317.
14. Rosenthal, U.; Pellny, P.-M.; Kirchbauer, F. G.; Burlakov, V. V. Acc. Chem. Res. 2000, 33, 119-129.
15. Barteau, M. A.; Madix, R. J. Surf. Sci. 1982, 120, 262-272.
16. For example, see: Jones, G. S.; Barteau, M. A.; Vohs, J. M. J. Phys. Chem. B 1999, 103, 1144-1151.
17. Low, J. J.; Goddard, W. A., III. J. Am. Chem. Soc. 1984, 106, 8321-8322.