Chemical Bonding in Three-Membered Ring Systems

The formation of the four 3-ring systems c-(CH<sub>2</sub>)<sub>3−<i>k</i></sub>(SiH<sub>2</sub>)<sub><i>k</i></sub> (<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"...

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Bibliographic Details
Main Authors: Nina Strasser, Alexander F. Sax
Format: Article
Language:English
Published: MDPI AG 2025-01-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/30/3/612
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Summary:The formation of the four 3-ring systems c-(CH<sub>2</sub>)<sub>3−<i>k</i></sub>(SiH<sub>2</sub>)<sub><i>k</i></sub> (<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><mi>k</mi><mo>=</mo><mn>0</mn></mrow></semantics></math></inline-formula>: cyclopropane, <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><mi>k</mi><mo>=</mo><mn>1</mn></mrow></semantics></math></inline-formula>: silirane, <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><mi>k</mi><mo>=</mo><mn>2</mn></mrow></semantics></math></inline-formula>: disilirane, <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><mi>k</mi><mo>=</mo><mn>3</mn></mrow></semantics></math></inline-formula>: cyclotrisilane) by addition of methylene and silylene to the double bond in ethene, disilene, and silaethene, as well as the elimination of the carbene analogs from the 3-rings, was studied with CAS(4,4) wave functions in both <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><msub><mi>C</mi><mrow><mn>2</mn><mi>v</mi></mrow></msub></semantics></math></inline-formula> and <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><msub><mi>C</mi><mi>s</mi></msub></semantics></math></inline-formula> symmetry. To reveal the charge and spin redistribution during these reactions the CAS(4,4) wave functions were analyzed using the orthogonal valence bond method (OVB). The potential energy curves, different internal coordinates, and the results of the OVB analysis show that, frequently, the addition and elimination reactions follow different minimum energy paths, because they are indeed diabatic reactions. In these cases, there are no energy barriers corresponding to saddle points on the potential energy surfaces but the energy increases during one diabatic reaction until, at a certain point, the system jumps to the other diabatic state and, in the following, the energy decreases. This happens for reactions in <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><msub><mi>C</mi><mrow><mn>2</mn><mi>v</mi></mrow></msub></semantics></math></inline-formula> symmetry; as soon as the system can change to the lower symmetry, the diabatic states combine to an adiabatic one and the reaction follows a single minimum energy path.
ISSN:1420-3049