title: Cyclooctyne-based reagents for uncatalyzed click chemistry: A computational survey.
abstract: With the goal of identifying alkyne-like reagents for use in click chemistry, but without Cu catalysts, we used B3LYP density function theory (DFT) to investigate the trends in activation barriers for the 1,3-dipolar cycloadditions of azides with various cyclooctyne, dibenzocyclooctyne, and azacyclooctyne compounds. Based on these trends, we find monobenzocyclooctyne-based reagents that are predicted to have dramatically improved reactivity over currently employed reagents.
authors.affiliation: Materials and Process Simulation Center, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA. wag@wag.caltech.edu.
authors.forename: Kimberly
authors.initials: K
authors.lastname: Chenoweth
authors.forename: David
authors.initials: D
authors.lastname: Chenoweth
authors.forename: William A
authors.initials: WA
authors.lastname: Goddard
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D034242:Cyclooctanes / Q000737:chemistry*; D007202:Indicators and Reagents
chemical_list: D000480:Alkynes; D001386:Azides; D034242:Cyclooctanes; D007202:Indicators and Reagents