The DOI matches its Crossref record; 9 of the 9 references it cites were found in a registry or an index.
Why Is Tetrazole Formation by Addition of Azide to Organic Nitriles Catalyzed by Zinc(II) Salts?
Abstract
The mechanism by which zinc(II) catalyzes the union of an azide ion with organic nitriles to form tetrazoles is investigated by means of density functional theory using the hybrid functional B3LYP. The calculations indicate that coordination of the nitrile to the zinc ion is the dominant factor affecting the catalysis; this coordination substantially lowers the barrier for nucleophilic attack by azide. Relative reaction rates of catalyzed and uncatalyzed tetrazole formation also provide experimental support for this conclusion.
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Cites
Density-functional thermochemistry. III. The role of exact exchange
Becke, A. D. (1993) · The Journal of Chemical Physics · doi:10.1063/1.464913 · Cited by 103,767
Density-functional exchange-energy approximation with correct asymptotic behavior
Becke, A. D. (1988) · Physical Review A · doi:10.1103/physreva.38.3098 · Cited by 53,711
Radul, O. M., Bukhanyuk, S. M., Rekhter, M. D., Zhungietu, G. I., & Ivanova, I. (1982) · Cited by 10,653
Barone, V., & Cossi, M. (1998) · The Journal of Physical Chemistry A · doi:10.1021/jp9716997 · Cited by 10,121
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(1984) · Elsevier eBooks · doi:10.1016/c2009-0-15932-9 · Cited by 3,151
Preparation of 5-Substituted 1 H-Tetrazoles from Nitriles in Water
Demko, Z. P., & Sharpless, K. B. (2001) · The Journal of Organic Chemistry · doi:10.1021/jo010635w · Cited by 971
Self-citationTheoretical Methods for the Description of the Solvent Effect in Biomolecular Systems
Orozco, M., & Luque, F. J. (2000) · Chemical Reviews · doi:10.1021/cr990052a · Cited by 622
Curran, D. P., Hadidaꝉ, S., & Kim, S. (1999) · Tetrahedron · doi:10.1016/s0040-4020(99)00458-5 · Cited by 142
Intramolecular Cycloadditions of Cyclobutadiene with Olefins
Limanto, J., Tallarico, J. A., Porter, J. R., Khuong, K. S., Houk, K. N., & Snapper, M. L. (2002) · Journal of the American Chemical Society · doi:10.1021/ja0203162 · Cited by 51
Cited by
Chanda, A., & Fokin, V. V. (2009) · Chemical Reviews · doi:10.1021/cr800448q · Cited by 1,534
Chen, X.-M., & Tong, M.-L. (2007) · Accounts of Chemical Research · doi:10.1021/ar068084p · Cited by 772
Noodleman, L., Lovell, T., Han, W.-G., Li, J., & Himo, F. (2004) · Chemical Reviews · doi:10.1021/cr020625a · Cited by 373
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Metadata
- Authors
- Himo, F., Demko, Z. P., Noodleman, L., & Sharpless, K. B.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-07-25
- Volume
- 125
- Issue
- 33
- Pages
- 9983-9987
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2068211209
- Cited by
- 353
- References
- 9
- FWCI
- 7.28
- Type
- journal article
- Language
- en
- Open access
- closed
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