The influence of intramolecular hydrogen bonding on the structure and E ↔ Z photoisomerization of urocanic acid derivatives

Frederick D. Lewis*, Beth A. Yoon

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The molecular structures and E ↔ Z photoisomerization reactions of methyl urocanate and several urocanamides were investigated. All of the Z isomers possess intramolecular hydrogen bonds. The intramolecular hydrogen bonds may influence the efficiency of photoisomerization but do not totally inhibit its occurrence. The relative energies of the electronic absorption of the E and Z isomers depends on the mode of hydrogen bonding and are accurately predicted in the case of methyl urocanate using INDO/S-CI calculations. The solvent dependence of the absorption spectra of methyl urocanate can be related to the effects of inter- and intramolecular hydrogen bonding.

Original languageEnglish (US)
Pages (from-to)749-763
Number of pages15
JournalResearch on Chemical Intermediates
Volume21
Issue number7
DOIs
StatePublished - Jul 1995

ASJC Scopus subject areas

  • Chemistry(all)

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