Experimental and theoretical study of the reactivity of a series of epoxides with chlorine atoms at 298 K

Literature Information

Publication Date 2021-02-19
DOI 10.1039/D0CP06033J
Impact Factor 3.676
Authors

Carmen M. Tovar, Alexander Haack, Ian Barnes, Iustinian Gabriel Bejan, Peter Wiesen


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Abstract

Evaluating the reactivity of epoxides in the gas phase is very important due to their wide distribution in the atmosphere, potential health implications and atmospheric impact. The kinetic rate constants for the oxidation of epoxides have been very little studied until now. From the experimental data obtained in this work has been observed that there is an increase in reactivity towards chlorine atoms as a CH2 group is added to the hydrocarbon chain. The Structure Activity Relationship (SAR) method usually provides a good approximation of the rate constant for a wide series of compounds especially for those without complex structure and multiple organic functions. However, a good determination of the factors included in SAR estimations depends largely on the database of these compounds, which in the case of epoxides is very limited. The SAR estimation method also does not take into account other possible factors that could affect reactivity, such as the geometry of the molecule. The aim of this work is to further evaluate the reactivity of epoxides with chlorine atoms using experimental determinations, theoretical calculations and SAR estimations. For this, rate coefficients have been measured at 298 ± 2 K and 1000 ± 4 mbar pressure of synthetic air in a 1080 l Quartz Reactor (QUAREC) and a 480 l Duran glass reactor for the reaction of chlorine atoms with cyclohexene oxide (CHO), 1,2-epoxyhexane (12EHX), 1,2-epoxybutane (12EB), trans-2,3-epoxybutane (tEB) and cis-2,3-epoxybutane (cEB). Theoretical calculations for the reactions studied are in good agreement with our experimental findings and provide insights about the position of the H atom abstraction and reactivity trends for a series of epoxides. The importance of taking into consideration the geometrical distribution and the ring influence to improve SAR calculations is discussed.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
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Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

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