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Title: A study of the interactions between ylidic phosphorus species and organic acids
Author: Lamb, Sarah
Awarding Body: Durham University
Current Institution: Durham University
Date of Award: 1998
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This thesis describes the synthesis and characterisation of phosphonium aryloxides, amides and phosphides. These compounds have been formed via the deprotonation of organic acids [of the type ROH, and R(_2)X, where X = NH, PH, R = aryl group] by basic phosphonium ylidic species [R(_3)PX, X = CH(_2,) C(Me)H, C(Ph)H, NH] in mixtures of hydrocarbon (toluene) and/or polar (acetonitrile, thf) solvents. All of these compounds contain both acidic CHs and 'naked' anions which promote extensive hydrogen bonding. Chapter 1 provides an outline of the fields of ylidic chemistry and hydrogen bonding. In Chapter 2, general experimental methods are described. Chapter 3 records all experimental results pertaining to this work. Here preparation of starting materials is documented, followed by an account of the synthesis and characterisation of twenty-three compounds. For all compounds melting point measurements, (^1)H NMR, (^31)P NMR, infrared spectra, and elemental analysis are recorded. Discussion of these results is documented in Chapters 4 to 7. Where possible, solid-state structures for compounds obtained by single crystal X-ray diffraction (nineteen structures) and single crystal neutron diffraction (two structures) are included. Chapter 4 discusses simple phosphonium aryloxide salts, while Chapter 5 is concerned with related phosphonium amides and phosphides. Chapter 6 deals with an extension of this work involving multifiinctional organic acids. Finally, Chapter 7 discusses unexpected results resulting from the work described in Chapter 6.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Hydrogen bonding; Phosphonium; Calixarene