Oligomerization Products from Thiamin in Methanol

dc.contributor.author Nishida, Clinton en_US
dc.contributor.department Chemistry en_US
dc.date.accessioned 2014-01-15T20:17:38Z
dc.date.available 2014-01-15T20:17:38Z
dc.date.issued 2014-01-15 en_US
dc.description.abstract In 1974, Shimahara, et al. [1 ] discovered that thiamin (vitamin B1 ) monochloride decomposes in alcohol solution, a reaction which cannot be accounted for solely on the basis of the known instability of thiamin in alkaline solution [2]. Of methanol, ethanol, and propanol, reaction in methanol led to the fastest decomposition rate. Reaction temperature, pH of the solution, and thiamin concentration affected the rate of reaction. For all alcohols, one of the products was determined by IR and NMR spectroscopy to be 5-(2-hydroxyethyl)-4-methyl-thiazole, the thiazole moiety of thiamin. The other product was a crystalline compound designated compound (X), or compound (X') if converted to the nitrate using silver nitrate. Initially believed to be the pentamer nitrate, penta-methi(1 ,4-dihydro-4-imino- 2-methyl-pyrimidinylen-1 ,5-amer nitrate (Fig. 1 a), based on NMR and mass spectral data, compound (X') has since been determined, via single crystal x-ray diffraction, to be the cyclic hexamer (Fig. 1 b, 2) by the Cramer group [4]. The cyclic tetramer has since been isolated and characterized as well (Fig. 1b) [5]. en_US
dc.format.extent ix, 92 pages en_US
dc.identifier.uri http://hdl.handle.net/10125/32152
dc.publisher University of Hawaii at Manoa en_US
dc.rights All UHM Honors Projects are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission from the copyright owner. en_US
dc.title Oligomerization Products from Thiamin in Methanol en_US
dc.type Term Project en_US
dc.type.dcmi Text en_US
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