The DOI matches its Crossref record; 83 of the 83 references it cites were found in a registry or an index.
Thiol–Ene Click Chemistry: Computational and Kinetic Analysis of the Influence of Alkene Functionality
Abstract
The influence of alkene functionality on the energetics and kinetics of radical initiated thiol-ene click chemistry has been studied computationally at the CBS-QB3 level. Relative energetics (ΔH°, ΔH(++), ΔG°, ΔG(++)) have been determined for all stationary points along the step-growth mechanism of thiol-ene reactions between methyl mercaptan and a series of 12 alkenes: propene, methyl vinyl ether, methyl allyl ether, norbornene, acrylonitrile, methyl acrylate, butadiene, methyl(vinyl)silanediamine, methyl crotonate, dimethyl fumarate, styrene, and maleimide. Electronic structure calculations reveal the underlying factors that control activation barriers for propagation and chain-transfer processes of the step-growth mechanism. Results are further extended to predict rate constants for forward and reverse propagation and chain-transfer steps (k(P), k(-P), k(CT), k(-CT)) and used to model overall reaction kinetics. A relationship between alkene structure and reactivity in thiol-ene reactions is derived from the results of kinetic modeling and can be directly related to the relative energetics of stationary points obtained from electronic structure calculations. The results predict the order of reactivity of alkenes and have broad implications for the use and applications of thiol-ene click chemistry.
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Cites
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A Correlation of Reaction Rates
Hammond, G. S. (1955) · Journal of the American Chemical Society · doi:10.1021/ja01607a027 · Cited by 3,559
The growing impact of click chemistry on drug discovery
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Using redundant internal coordinates to optimize equilibrium geometries and transition states
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The growing applications of click chemistry
Moses, J. E., & Moorhouse, A. D. (2007) · Chem. Soc. Rev. · doi:10.1039/b613014n · Cited by 2,367
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Copper-free click chemistry for dynamic in vivo imaging
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Cu-free click cycloaddition reactions in chemical biology
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Inertia and driving force of chemical reactions
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Cited by
Lowe, A. B. (2014) · Polym. Chem. · doi:10.1039/c4py00339j · Cited by 768
Photopolymerizable Biomaterials and Light-Based 3D Printing Strategies for Biomedical Applications
Yu, C., Schimelman, J., Wang, P., Miller, K. L., Ma, X., You, S., Guan, J., Sun, B., Zhu, W., & Chen, S. (2020) · Chemical Reviews · doi:10.1021/acs.chemrev.9b00810 · Cited by 579
Thiol–Ene Clickable Gelatin: A Platform Bioink for Multiple 3D Biofabrication Technologies
Bertlein, S., Brown, G., Lim, K. S., Jungst, T., Boeck, T., Blunk, T., Tessmar, J., Hooper, G. J., Woodfield, T. B. F., & Groll, J. (2017) · Advanced Materials · doi:10.1002/adma.201703404 · Cited by 331
Metadata
- Authors
- Northrop, B. H., & Coffey, R. N.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-08-08
- Volume
- 134
- Issue
- 33
- Pages
- 13804-13817
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2334127072
- Cited by
- 323
- References
- 83
- FWCI
- 7.14
- Type
- journal article
- Language
- en
- Open access
- closed
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