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EPR study of radicals derived from fumaronitrile and related carboxylic acids

✍ Scribed by Peter Smith; William H. Donovan; Julie K. Parker

Publisher
John Wiley and Sons
Year
1989
Tongue
English
Weight
887 KB
Volume
27
Category
Article
ISSN
0749-1581

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✦ Synopsis

Using aqueous TiCI,-based continuous-flow, radical-generating methods, a comprehensive investigation was made of radicals derived from fumaronitrile and cis-and trans-carboxylic acids of general structure CY(COOH)=CH(COOH), where Y is H, CH, or CH,COOH. All substrates were examined at 25°C but, where appropriate, the temperature was also varied over the range 1040 "C. The radicals observed from these compounds were of two main types, addition and electron transfer. This investigation emphasized the study of the addition radicals formed from fumaronitrile and maleic acid and of the electron-transfer radicals formed from the carboxylic acids. Several of the addition radicals showed long-range s littin Among these, the radicals lar attention, thus showing that they exist in axial and equatorial conformations-a situation not commonly encountered. All of the acids yielded one-electron transfer radicals, some of which had interesting stereochemical properties, including intramolecular hydrogen bonding. 'CH(CH)CH(CN)kHOCH,CH,OkH, and *CH(COOH)CH(COOH)CHOCH~CH20 -H, were given particu-KEY WORDS EPR Fumaronitrile Butenedioic acids Addition and electron-transfer radicals INDO-MO calculations Axial and equatorial conformations Intramolecular hydrogen bonding '[(HOOC)CH=CH(COOH)] -+ H + -+ '[(HOOC)CH=CH(COOH)]H

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