Thiol‐Ene Coupling Reaction for Functionalization of Nonactivated Alkenes: Mechanism and Mathematical Model Article Swipe
Laureana R. Soria
,
Mara L. Polo
,
Victoria A. Vaillard
,
David A. Echeverri
,
M. Spontón
,
Santiago E. Vaillard
,
Luis A. Ríos
,
Diana A. Estenoz
,
Gregorio R. Meira
·
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.1002/slct.202501136
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.1002/slct.202501136
This article is a continuation of Polo et al. In that article, we investigated the synthesis of an aminated methyl oleate through a photoinitiated thiol‐ene coupling reaction between cysteamine hydrochloride and cis methyl oleate in the presence of a photoinitiator. The present article develops a mathematical model for simulating Experiment 11 of Polo et al. The new model extends the reaction mechanism proposed by Chatgilialoglu et al. to enable generation of high molar mass by‐products; and it contains 16 kinetic constants. Nine of that constants were directly adopted from literature, five other constants were estimated from reduced ad hoc experiments, and the last two constants were estimated by fitting the complete model predictions to the available measurements. The model adequately predicts the normalized 1 H‐NMR areas due to vinyl protons, the final weight‐average molar mass, and the final concentration of desired product. The simulation results suggest an almost constant concentration of dissolved cysteamine along the reaction, and a rapid isomerization of the cis methyl oleate reagent into the trans‐ isomer. The desired product is generated following an approximately zero‐order kinetics. The generation of both low‐ and high‐molar mass by‐products reduces the selectivity of the reaction toward the desired product.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1002/slct.202501136
- https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/slct.202501136
- OA Status
- bronze
- References
- 40
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4412116293
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- OpenAlex ID
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https://openalex.org/W4412116293Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1002/slct.202501136Digital Object Identifier
- Title
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Thiol‐Ene Coupling Reaction for Functionalization of Nonactivated Alkenes: Mechanism and Mathematical ModelWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2025Year of publication
- Publication date
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2025-07-01Full publication date if available
- Authors
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Laureana R. Soria, Mara L. Polo, Victoria A. Vaillard, David A. Echeverri, M. Spontón, Santiago E. Vaillard, Luis A. Ríos, Diana A. Estenoz, Gregorio R. MeiraList of authors in order
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https://doi.org/10.1002/slct.202501136Publisher landing page
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https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/slct.202501136Direct link to full text PDF
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YesWhether a free full text is available
- OA status
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bronzeOpen access status per OpenAlex
- OA URL
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https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/slct.202501136Direct OA link when available
- Concepts
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Ene reaction, Surface modification, Thiol, Mechanism (biology), Coupling reaction, Coupling (piping), Chemistry, Combinatorial chemistry, Materials science, Organic chemistry, Catalysis, Physical chemistry, Philosophy, Epistemology, MetallurgyTop concepts (fields/topics) attached by OpenAlex
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0Total citation count in OpenAlex
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40Number of works referenced by this work
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10Other works algorithmically related by OpenAlex
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| abstract_inverted_index.concentration | 139, 150 |
| abstract_inverted_index.hydrochloride | 30 |
| abstract_inverted_index.isomerization | 160 |
| abstract_inverted_index.measurements. | 117 |
| abstract_inverted_index.Chatgilialoglu | 65 |
| abstract_inverted_index.by‐products; | 75 |
| abstract_inverted_index.photoinitiated | 24 |
| abstract_inverted_index.photoinitiator. | 40 |
| abstract_inverted_index.weight‐average | 133 |
| cited_by_percentile_year | |
| countries_distinct_count | 2 |
| institutions_distinct_count | 9 |
| citation_normalized_percentile.value | 0.19258479 |
| citation_normalized_percentile.is_in_top_1_percent | False |
| citation_normalized_percentile.is_in_top_10_percent | False |