Structural Chemistry

, Volume 3, Issue 4, pp 277–289 | Cite as

Electronic absorption and fluorescence spectra and excited singlet-state dipole moments of biologically important pyrimidines

  • Cyril Párkányi
  • Christian Boniface
  • Jean-Jacques Aaron
  • Mame Diabou Gaye
  • Ratna Ghosh
  • László von Szentpály
  • Krishnan S. RaghuVeer


Electronic absorption and fluorescence emission spectra of several biologically important pyrimidines were measured at room temperature (298 K) in the following solvents: dioxane, ethyl ether, chloroform, ethyl acetate, 1-butanol, 2-propanol, methanol, dimethylformamide, acetonitrile, and dimethyl sulfoxide. The compounds studied were uracil, thymine, cytosine, 5-fluorouracil, 5-chlorouracil, 5-bromouracil, 5-iodouracil, 2-thiouracil, barbituric acid, and orotic acid. In combination with the ground-state dipole moments of the above compounds, these spectral data were used to determine their lowest excited singlet-state dipole moments using the soivatochromic method. The effects of the solvent upon the spectral properties and of the structure upon the ground and excited singlet-state dipole moments are discussed. For most of the compounds, the excited singlet-state dipole moments are higher than their ground-state counterparts.

The theoretical dipole moments for all the pyrimidines listed above, as well as for pyrimidine, alloxan, and uracil-5-carboxylic acid, were calculated by two methods. One approach involved a combination of the PPP (π-LCI-SCF-MO) method for the π-contribution to the overall dipole moment and the σ-contribution obtained as a vector sum of the σ-bond moments and group moments. The second set of theoretical values was obtained by the CNDO/2 method. The results were compared with the experimental dipole moments.


Dipole Moment Pyrimidine Uracil Barbituric Thymine 
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Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • Cyril Párkányi
    • 1
  • Christian Boniface
    • 1
  • Jean-Jacques Aaron
    • 2
  • Mame Diabou Gaye
    • 2
  • Ratna Ghosh
    • 3
  • László von Szentpály
    • 3
  • Krishnan S. RaghuVeer
    • 4
  1. 1.Department of ChemistryFlorida Atlantic UniversityBoca RatonUSA
  2. 2.Laboratoire de Chimie Organique Physique, Institut de Topologie et de Dynamique des Systèmes [Associé au CNRS]Université Paris VIIParisFrance
  3. 3.Department of ChemistryUniversity of the West IndiesKingston 7Jamaica
  4. 4.Center for Photochemical SciencesBowling Green State UniversityBowling GreenUSA

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