Graduate Program

Chemistry

Degree Name

Master of Science (MS)

Semester of Degree Completion

2012

Thesis Director

Kraig A. Wheeler

Thesis Committee Member

Edward M. Treadwell

Thesis Committee Member

Daniel J. Sheeran

Thesis Committee Member

Mark E. McGuire

Abstract

The area of supramolecular chemistry seeks to understand the organization of molecular structures and the interactions that hold such assemblies together by non-covalent interactions such as electrostatic, hydrogen bonding, π-π stacking interactions, and hydrophobic or solvatophobic effects. One such example that comes under supramolecular chemistry is the phenyl embrace interaction. These interactions occur due to the cooperative participation of at least three or more neighboring phenyl groups arranged as an interlocking propeller configuration to give complementary edge-to-face or offset face-to-face interactions. In order to understand the effect of functional groups on the tendencies of organic compounds to form phenyl embrace interactions, a family of trityloxy and tritylamino derivatives was synthesized and solid-state structures studied. While earlier investigations carried by Scudder and Dance focused primarily on higher incidences of six or eight-fold phenyl embrace interactions, the current work is dedicated in exploring the symmetry requirements and tendencies on the least possible phenyl embrace interactions such as four-fold and especially three-fold phenyl embrace interaction; which remained elusive so far in the field of phenyl embrace. Results from this study highlight the importance of phenyl embrace interactions. Exploring the structural features of new systems, combined with a search of the existing structures, provides a unique opportunity to probe the molecular recognition profile of this intermolecular contact involving neighboring phenyl groups.

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