Interfacial behavior of uracil derivatives

James G. Bake, Sherril D. Christian, M. H. Kim, Glenn Dryhurst

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

The adsorption of a number of methylated uracil derivatives and of 5-fluorouracil has been studied by surface electrochemical methods at a mercury electrode. All derivatives exhibit an initial or dilute adsorption region where they are adsorbed flat on the electrode surface and are bound by π-electron overlap with the electrode. Uracil, thymine, 1,5-dimethyl-uracil, 5,6-dimethyluracil, 1,5,6-trimethyluracil and 5-fluorouracil undergo a surface reorientation from the initial flat solution activities for each compound. An unsubstituted N(3)-H group is an absolute requirement for a uracil derivative to be capable of adopting the perpendicular surface stance. In the perpendicular orientation the uracil derivative appears to be bound to the electrode primarily via a N(3)-H--(-) electrode bond although a similar but weaker hydrogen bond can be formed via the N(1)-H group for certain compounds.

Original languageEnglish (US)
Pages (from-to)355-367
Number of pages13
JournalBiophysical Chemistry
Volume9
Issue number4
DOIs
StatePublished - May 1979
Externally publishedYes

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Organic Chemistry

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