Date of Award

2012

Degree Name

Chemistry

College

College of Science

Type of Degree

M.S.

Document Type

Thesis

First Advisor

Michael Castellani

Second Advisor

John Hubbard

Third Advisor

Robert Morgan

Abstract

This thesis reports the synthesis of an organic molecule, 1,4-bis(2,3,4,5-tetramethylcyclopentadienyl)butane by two different methods, in about 75% and 85% crude yield. Deprotonation of this molecule followed by reaction with FeCl2 generated the tethered ferrocene, [4]octamethylferrocenophane. Although the yield was low in the first attempt (2%), this molecule has been characterized through NMR spectroscopy, X-ray crystallography, electronic spectroscopy, elemental analysis, and decomposition temperature. A computational study was performed to determine the energy gap between each minimum energy structure. It was found that the energy barrier was not high enough to prevent a rapid interconversion between the two structures of minimum energy on the NMR time scale. The attempted syntheses of both 1,1'-(tetramethylene)ferrocenium tetracyanoethanide and 1,1'-(tetramethylene)cobaltocenium hexafluorophosphate are also reported, although the identity of neither compound has been confirmed.

Subject(s)

Molecules.

Chemistry, Inorganic.

Chemistry, Organic.

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