Thesis (Ph. D.)--Washington State University, May 2009. / Title from PDF title page (viewed on Apr. 19, 2010). "College of Pharmacy." Includes bibliographical references.

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x, 154 leaves : ill. ; 29 cm Typescript. (Another copy on microfilm is located in Archives) Thesis (Ph.D.)--University of Oregon Vita Bibliography: leaves 144-154

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Various chromone derivatives have been used in asthma therapy, and their biological activity is apparently related to certain chemical features which include conformation and acidity. In the present study, substituent effects on conformation and acidity have been explored in chromone systems with potential biological activity. A range of variously substituted symmetrical chromone-2-carboxamides (including a series of N,N-dimethylchromone-2-carboxamides) have been prepared via chromone-2-carboxylic acids, which, in turn, were prepared from the corresponding o-hydroxyacetophenones. The N,N-dimethylchromone-2-carboxamides were prepared by reacting the appropriate chromone-2-carbonyl chlorides with dimethylammonium chloride in pyridine, in an approach which resolved various problems encountered in the preparation of these compounds. Substituent effects on the conformation of chromone-2-carboxamides have been explored using dynamic NMR spectroscopy, and the observed splitting of the N-alkyl signals has been attributed to slow site-exchange of the N-alkyl substituents. Dynamic NMR frequency separations and coalescence temperatures have been used to calculate rotational energy barriers, and substituent effects on these rotational energy barriers have been analysed. The possible implication of ring-opening of chromones in chromone pharmacology has also been examined. A range of 3-(2-hydroxybenzoyl)acrylamides has been prepared via the dimethylamine-mediated ring-opening of N,N-dimethylchromone-2-carboxamides and the E-double-bond configuration of the ring-opened products has been unambiguously established by single crystal analysis of the parent system. The configuration and conformation of the crystal structure of the parent system have been shown, using IR and NMR spectroscopic, and molecular graphics techniques, to be maintained in solution and to characterise the whole series. ¹H and ¹³C NMR spectroscopy have also been used to study the dimethylamine-mediated ring-opening of disodium cromoglycate. The kinetics of the dimethylamine-mediated ring-opening of N,N-dimethylchromone-2-carboxamides have been studied using UV spectroscopy. These reactions have been shown to follow third-order kinetics overall and a mechanism accommodating the observed third-order kinetics has been proposed. Substituent effects have been further investigated by the potentiometric determination of the pKa (pK [subscript a]) values for a series of chromone-2-carboxylic acids. The relationship between acidity and the observed rate constants has been explored and has verified that the observed rate constants are sensitive to the influence of meta-substituents on the stability of the phenoxide ion "leaving group" rather than C-2 electrophilicity.

Even though early man did not know the nature of coloring matter in flowers, he used the coloring matter as dye for centuries. There are a variety of reasons for the interest of chemists in natural and artificial coloring matters. One of these is the color pleasure, anothe1· is the commercial importance. The visible color facilitates the experimental work in the search for methods if separation, purification and determination of organic structures. Search for the knowledge of coloring matter goes far back in history. Man has dyed his textiles with the help of mordants from the most ancient times up to the time of Perkin's discovery of mauve. Then a new era in dyestuff chemistry commenced. In the first half of the nineteenth century with the rise and development of the study of Organic chemistry much attention was directed to the extraction and characterization of pure coloring matters from natural sources .... usually the bark, leaves, fruits. or sap of trees or plants. During the twentieth century -- and just a little before that--great progress has been made in the synthesis of many typical natural coloring matters and the improved technique and novel synthetical methods which will bear upon the general progress of chemistry. This research was done with the purpose of isolating and identifying the coloring matter in the flowers of Vinca Major, with the common name of periwinkle. This was done by extracting the pigment of the flowers with methanol, amyl alcohol, and crystallizing the pigment as a chloride. For this pigment, solubility, color reactions, spectra and other physical properties were obtained.

The pigment-lipid complexes of the phytopathogen, Xanthomonas juglandis, were studied. Experiments were designed to determine the cellular location of the complexes and whether or not they are associated with protein.

Separation of the pigment-lipid esters of Xanthomonas juglandis (campestris) in a silica gel G:celite 545 column yielded 4 bands. Two of these bands, ester #1 and #2, make up over 95% of the mixture. Analysis of the four pigments indicate that three are phospholipids and that the phosphate accounts for about 3-4% of the weight of each of the two major esters.

This study is a report of the results of a series of experiments, the purposes of which were to determine: (1) what natural pigments are available in Denton County, Texas, (2) the variety, quality, and quantity of the native pigments as compared with standard commercial pigments, and (3) the suitability of these native pigments for use in the preparation of artists' colors. Since the chief interest was in the specific hues, their quality and variety, the factor of commercial possibilities was not investigated.