A DFT study of uracil and 5-bromouracil in nanodroplets

Tanja van Mourik, Victor I. Danilov, Vladimir V. Dailidonis, Noriyuki Kurita, Hajime Wakabayashi, Takayuki Tsukamoto

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29 Citations (Scopus)

Abstract

The canonical (keto) and rare (enol) tautomers of uracil and 5-bromouracil in clusters comprising 50 and 100 water molecules (nanodroplets) were studied using density functional theory. The geometries of the various complexes were optimized at two different levels of theory, BLYP/6-31G(d,p) and B3LYP/6-31G(d,p). Tautomerization energies were computed using the BLYP, B3LYP and M05-2X density functionals. The gas-phase tautomerization energies of uracil and 5-bromouracil are very similar, favoring the keto tautomer. However, in the hydrated phase, the tautomeric preference of 5-bromouracil is reversed. This result is obtained for all four sets of clusters (BLYP or B3LYP optimized, containing 50 or 100 water clusters) and at all levels of theory employed, and indicates that a bromine atom in the 5-position considerably increases the proportion of the hydroxyl group present in uracil.

Original languageEnglish
Pages (from-to)233-244
Number of pages12
JournalTheoretical Chemistry Accounts
Volume125
Issue number3-6
DOIs
Publication statusPublished - Mar 2010

Keywords

  • Mutagenicity
  • Uracil
  • 5-Bromouracil
  • Water cluster
  • DFT
  • Tautomerization
  • POLARIZABLE CONTINUUM MODEL
  • CIRCULAR-DICHROISM SPECTRA
  • NUCLEIC-ACID BASES
  • ALANINE N'-METHYLAMIDE
  • RAMAN OPTICAL-ACTIVITY
  • DIFFUSION MONTE-CARLO
  • AB-INITIO
  • DENSITY FUNCTIONALS
  • AQUEOUS-SOLUTION
  • VIBRATIONAL ABSORPTION

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