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Noncovalent interactions involving aromatic rings: How to identify and isolate π–π, CH–π, and NH–π attractions

Emenike, Bright Ugochukwu
http://rave.ohiolink.edu/etdc/view?acc_num=miami1312996577

Abstract Details

2011, Doctor of Philosophy, Miami University, Chemistry and Biochemistry.
Noncovalent weak interactions associated with aromatic rings, such as π–π, CH–π and NH–π, have been identified and studied experimentally in solution and in the solid state. Triptycene-derived model compounds were used as conformation equilibrium reporters for the direct quantification of these interactions. For arene-arene interactions, the effect of substituent position on the strength of the π–π stacking interaction was studied. Using a set of α-substituted acetates at the C1 position of the triptycene model, a direct substituent-arene interaction is hypothesized, but a CH–π interaction was observed instead; the effect of the substituents on the interaction was studied. NH–π interaction between an sp2-hybridized N atom and a phenyl ring was also studied, along with the effect of substituent groups on both the acidity of the –NH groups and electron density of the phenyl π system. The latter study led to the development of a combined computational and proton-NMR based technique for the determination of the –NH acidities.
Benjamin Gung, PhD (Advisor)
Richard Taylor, PhD (Committee Chair)
C. Scott Hartley, PhD (Committee Member)
Neil Danielson, PhD (Committee Member)
Marvin Thrash, PhD (Committee Member)
198 p.
Chemistry; Organic Chemistry
triptycene; noncovalent interactions; aromatic ring; substitutent effect

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Citations

  • Emenike, B. U. (2011). Noncovalent interactions involving aromatic rings: How to identify and isolate π–π, CH–π, and NH–π attractions [Doctoral dissertation, Miami University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=miami1312996577

    APA Style (7th edition)

  • Emenike, Bright. Noncovalent interactions involving aromatic rings: How to identify and isolate π–π, CH–π, and NH–π attractions. 2011. Miami University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=miami1312996577.

    MLA Style (8th edition)

  • Emenike, Bright. "Noncovalent interactions involving aromatic rings: How to identify and isolate π–π, CH–π, and NH–π attractions." Doctoral dissertation, Miami University, 2011. http://rave.ohiolink.edu/etdc/view?acc_num=miami1312996577

    Chicago Manual of Style (17th edition)

miami1312996577
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© 2011, all rights reserved.
This open access ETD is published by Miami University and OhioLINK.