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Thesis Sobieski Final 2.1.pdf (1.73 MB)

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Assessing steric bulk of protecting groups via a computational determination of exact cone angle and exact solid cone angle

Sobieski, Julian Witold
http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1528385706530151

Abstract Details

2018, BS, Kent State University, College of Arts and Sciences / Department of Chemistry and Biochemistry.
The exact cone angles and exact solid angles for 60 organic protecting groups were calculated and compared to previous methods of steric bulk approximation. Due to the lack of steric descriptors in literature for organic protecting groups, there was a need to develop a new approach. Recently reported computational techniques using Mathematica packages FindConeAngle and FindSolidAngle have allowed for the rigorous computation of several organic protecting group families. Functionalities analyzed by this method include, but are not limited to, silyl, acetal, halogenated, and aromatic protecting groups. Using Spartan '16, the approach uses equilibrium-optimized (B3LYP/LANL3DZ) structures of organic protecting groups coordinated to a single Pd atom in place of the protected O/N. Experimental evidence from a systematic study of steric influence by protecting groups on the synthetic yield of the Mitsunobu reaction is confirmed to correlate with the steric descriptors proposed in this work. The null conformation of equilibrium-optimized protecting groups is proposed as a concept for computationally determining the native behavior of organic protecting groups, the inclusion of which bears significance for computed steric bulks.
Scott Bunge, Dr. (Advisor)
Mietek Jaroniec, Dr. (Committee Member)
Paul Sampson, Dr. (Committee Member)
Maxim Dzero, Dr. (Committee Member)
100 p.
Chemistry
Steric, bulk, descriptor, computational, organic, protecting, exact, solid, cone, angle, Tolman,

Recommended Citations

Citations

  • Sobieski, J. W. (2018). Assessing steric bulk of protecting groups via a computational determination of exact cone angle and exact solid cone angle [Undergraduate thesis, Kent State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1528385706530151

    APA Style (7th edition)

  • Sobieski, Julian. Assessing steric bulk of protecting groups via a computational determination of exact cone angle and exact solid cone angle . 2018. Kent State University, Undergraduate thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1528385706530151.

    MLA Style (8th edition)

  • Sobieski, Julian. "Assessing steric bulk of protecting groups via a computational determination of exact cone angle and exact solid cone angle ." Undergraduate thesis, Kent State University, 2018. http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1528385706530151

    Chicago Manual of Style (17th edition)

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This open access ETD is published by Kent State University Honors College and OhioLINK.