doi: 10.1021/ja030204q.
Why is tetrazole formation by addition of azide to organic nitriles catalyzed by zinc(II) salts?
Affiliations
- PMID: 12914461
- DOI: 10.1021/ja030204q
Item in Clipboard
Why is tetrazole formation by addition of azide to organic nitriles catalyzed by zinc(II) salts?
J Am Chem Soc.
.
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.
Similar articles
-
Mechanisms of tetrazole formation by addition of azide to nitriles.J Am Chem Soc. 2002 Oct 16;124(41):12210-6. doi: 10.1021/ja0206644. J Am Chem Soc. 2002. PMID: 12371861
-
Synthesis of 5-substituted 1H-tetrazoles by the copper-catalyzed [3+2] cycloaddition of nitriles and trimethylsilyl azide.Chem Asian J. 2008 Sep 1;3(8-9):1575-80. doi: 10.1002/asia.200800085. Chem Asian J. 2008. PMID: 18561350
-
Mechanistic insights on azide-nitrile cycloadditions: on the dialkyltin oxide-trimethylsilyl azide route and a new Vilsmeier-Haack-type organocatalyst.J Am Chem Soc. 2011 Mar 30;133(12):4465-75. doi: 10.1021/ja109700b. Epub 2011 Mar 7. J Am Chem Soc. 2011. PMID: 21381737
-
Cu-catalyzed azide-alkyne cycloaddition.Chem Rev. 2008 Aug;108(8):2952-3015. doi: 10.1021/cr0783479. Chem Rev. 2008. PMID: 18698735 Review. No abstract available.
-
Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions.Chem Soc Rev. 2007 Oct;36(10):1674-89. doi: 10.1039/b701444a. Epub 2007 Jun 12. Chem Soc Rev. 2007. PMID: 17721589 Review.
Cited by
-
Greener Selective Cycloalkane Oxidations with Hydrogen Peroxide Catalyzed by Copper-5-(4-pyridyl)tetrazolate Metal-Organic Frameworks.Molecules. 2015 Oct 21;20(10):19203-20. doi: 10.3390/molecules201019203. Molecules. 2015. PMID: 26506333 Free PMC article.
-
Supramolecular Cu(ii) nanoparticles supported on a functionalized chitosan containing urea and thiourea bridges as a recoverable nanocatalyst for efficient synthesis of 1H-tetrazoles.RSC Adv. 2023 Sep 11;13(39):27088-27105. doi: 10.1039/d3ra01989f. eCollection 2023 Sep 8. RSC Adv. 2023. PMID: 37701273 Free PMC article.
-
Nanomaterial catalyzed green synthesis of tetrazoles and its derivatives: a review on recent advancements.RSC Adv. 2021 Dec 7;11(62):39058-39086. doi: 10.1039/d1ra05955f. eCollection 2021 Dec 6. RSC Adv. 2021. PMID: 35492456 Free PMC article. Review.
-
Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new ZnO nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions.Sci Rep. 2022 Jun 24;12(1):10723. doi: 10.1038/s41598-022-13011-9. Sci Rep. 2022. PMID: 35750767 Free PMC article.
-
Synthesis of N3-substituted carboranyl thymidine bioconjugates and their evaluation as substrates of recombinant human thymidine kinase 1.Eur J Med Chem. 2013 Feb;60:456-68. doi: 10.1016/j.ejmech.2012.11.041. Epub 2012 Dec 5. Eur J Med Chem. 2013. PMID: 23318906 Free PMC article.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Other Literature Sources
