Collect. Czech. Chem. Commun. 1994, 59, 951-956

Intramolecular Hydrogen Bonds and Fermi Resonance in N-Substituted N'-(2-Fluorobenzoyl)thiourea Derivatives

Oľga Hritzová and Dušan Koščík

Department of Organic Chemistry, Šafárik University, 041 67 Košice, Slovak Republic


The presence of intramolecular NH...O=C bonds was proved in N-substituted N'-(2-fluorobenzoyl)thiourea derivatives by analysis of their infrared spectra. The intramolecular vibrational effects bring about a shift of the ν(NH) vibrational band to lower frequencies to the extent that the band gets into a vicinity to the δ(NH) overtone and Fermi resonance occurs between them. In addition, the ν(NH) vibration is also affected by Fermi resonance with the ν(CO) + δ(NH) combination. Double absorption bands were observed in the ν(CO) region for some of the derivatives. Based on perturbation theory applied to three-level interactions and using the Langseth and Lord equations, the band frequencies corrected for Fermi resonance were calculated and the hydrogen bond strength was examined in the compounds studied.