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Structure and reactivity of selected binaphthyl derivatives
Author(s)
Kabwit, Rodriguez Yav
Date Issued
2013
Type
Thesis
Publisher
Cape Peninsula University of Technology
Abstract
In this thesis, the complexation behaviour of the host compounds, 1,1’-binaphthyl-
2,2’-dicarboxylic acid (BNDA) and 1,1’-binaphthyl-2,2’-diol (BINOL) were
investigated. These hosts are large, bulky and scissor shaped; they contain
functionalities to selectively interact with other molecules. A series of small organic
compounds, particularly amines, were used in the preparation of the complexes.
BNDA formed three complexes with acyclic amines, two complexes with the cyclic
amines and two complexes with a racemic amine in different solvents.
All the complexes formed were salts. The amines used were diethylamine, di-nbutylamine,
cyclohexylamine, dicyclohexylamine, and sec-butylamine. For the
studies with the acyclic amines and cyclic amines, crystals were grown in methanol
as a co-solvent.
Similar experiments were conducted with BINOL. Successful complexation only
occurred with cyclohexylamine and dicyclohexylamine respectively. An amine host,
1,1’-binaphthyl-2,2’- diamine (BINDIA) was also considered with acidic and amide
guests to extend the study of the binaphthyl derivatives, but from the array of guests
used, the host only formed an inclusion compound with dimethylacetamide (DMA).
The structures of all the complexes were elucidated using single crystal X-ray
diffraction. Thermal analysis was performed in order to determine the thermal
stability of the complexes, including techniques such as thermogravimetry,
differential scanning calorimetry and hot stage microscopy. The kinetics of
desolvation was investigated for some of the complexes.
2,2’-dicarboxylic acid (BNDA) and 1,1’-binaphthyl-2,2’-diol (BINOL) were
investigated. These hosts are large, bulky and scissor shaped; they contain
functionalities to selectively interact with other molecules. A series of small organic
compounds, particularly amines, were used in the preparation of the complexes.
BNDA formed three complexes with acyclic amines, two complexes with the cyclic
amines and two complexes with a racemic amine in different solvents.
All the complexes formed were salts. The amines used were diethylamine, di-nbutylamine,
cyclohexylamine, dicyclohexylamine, and sec-butylamine. For the
studies with the acyclic amines and cyclic amines, crystals were grown in methanol
as a co-solvent.
Similar experiments were conducted with BINOL. Successful complexation only
occurred with cyclohexylamine and dicyclohexylamine respectively. An amine host,
1,1’-binaphthyl-2,2’- diamine (BINDIA) was also considered with acidic and amide
guests to extend the study of the binaphthyl derivatives, but from the array of guests
used, the host only formed an inclusion compound with dimethylacetamide (DMA).
The structures of all the complexes were elucidated using single crystal X-ray
diffraction. Thermal analysis was performed in order to determine the thermal
stability of the complexes, including techniques such as thermogravimetry,
differential scanning calorimetry and hot stage microscopy. The kinetics of
desolvation was investigated for some of the complexes.
Additional information
Thesis (MTech (Chemistry))--Cape Peninsula University of Technology, 2013
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