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The Role of Ring Strain in the Reactivity of Transition Metal-Catalyzed C–C Bond Activation Reactions

Ahlstrom, Tyler (2022) The Role of Ring Strain in the Reactivity of Transition Metal-Catalyzed C–C Bond Activation Reactions. Master's Thesis, University of Pittsburgh. (Unpublished)

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Cyclic alkanes and ketones are common starting materials in transition metal-catalyzed C–C bond activation reactions because their ring strain provides the thermodynamic driving force of the otherwise challenging C–C bond cleavage step. A computational study was performed to investigate the factors affecting the thermodynamics and kinetics of transition-metal-catalyzed C–C bond activation reactions of cyclic alkanes and ketones. The results show that while the reaction energies and rates are strongly affected by the release of ring strain and, in the case of ketones, metal-carbonyl back-bonding, the rates are also affected by steric environment of the C–C bond prior to activation. Linear structure-activity relationships are explored for these factors and quantitatively compared for Ni-, Rh-, and Ir-based catalysts, and for cyclic reactants with three-, four-, and five-membered rings.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Ahlstrom, Tylertylerahlstrom@gmail.comtma29
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairLiu,
Committee MemberHutchison,
Committee MemberMeyer,
Date: 6 June 2022
Date Type: Publication
Defense Date: 20 January 2022
Approval Date: 6 June 2022
Submission Date: 16 March 2022
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 60
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: ring strain, metallacycle, transition-metal catalyst
Date Deposited: 06 Jun 2022 15:58
Last Modified: 06 Jun 2022 15:58


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