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
Hoyle, C. E., & Bowman, C. N. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.200903924 · Cited by 4,182
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
Kolb, H. C., & Sharpless, K. B. (2003) · Drug Discovery Today · doi:10.1016/s1359-6446(03)02933-7 · Cited by 3,148
Petersson, G. A., & Al-Laham, M. A. (1991) · The Journal of Chemical Physics · doi:10.1063/1.460447 · Cited by 3,098
Using redundant internal coordinates to optimize equilibrium geometries and transition states
Peng, C., Ayala, P. Y., Schlegel, H. B., & Frisch, M. J. (1996) · Journal of Computational Chemistry · doi:10.1002/(sici)1096-987x(19960115)17:1<49::aid-jcc5>3.0.co;2-0 · Cited by 2,749
The growing applications of click chemistry
Moses, J. E., & Moorhouse, A. D. (2007) · Chem. Soc. Rev. · doi:10.1039/b613014n · Cited by 2,367
Hein, J. E., & Fokin, V. V. (2010) · Chemical Society Reviews · doi:10.1039/b904091a · Cited by 2,198
Copper-free click chemistry for dynamic in vivo imaging
Baskin, J. M., Prescher, J. A., Laughlin, S. T., Agard, N. J., Chang, P. V., Miller, I. A., Lo, A., Codelli, J. A., & Bertozzi, C. R. (2007) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0707090104 · Cited by 1,833
Cu-free click cycloaddition reactions in chemical biology
Jewett, J. C., & Bertozzi, C. R. (2010) · Chemical Society Reviews · doi:10.1039/b901970g · Cited by 1,684
Inertia and driving force of chemical reactions
Evans, M. G., & Polanyi, M. (1938) · Transactions of the Faraday Society · doi:10.1039/tf9383400011 · Cited by 1,679
Cited by
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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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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
