Combined matrix-isolation FT-IR and ab-initio 6-31++G** studies on tautomeric properties of nucleic acid bases and simpler model molecules

Linda Houben, Kristien Schoone, Johan Smets, Ludwik Adamowicz, Guido Maes

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The combined matrix isolation/ab initio 6-31++G** method is used to study the tautomeric equilibria of purine, 1-CH3-adenine, 3-CH3-adenine and N-CH3-adenine in isolated conditions. For the N9H ⇆ N7H prototropism, tautomeric equilibrium constants of 0.085, 0.090 and 0.005 are obtained for purine, 1-CH3-adenine and N-CH3-adenine, respectively. The other prototropic equilibria that are considered are the amino ⇆ imino tautomerism for which relative amounts of 5.5% for the rare amino form in 1-CH3-adenine and 0.5% for the minor imino tautomer of 3-CH3 adenine were observed, and the N9H ⇆ N3H prototropism where only 0.7% of the experimental spectrum could be accounted for by the presence of the less stable N3H form in N-CH3-adenine.

Original languageEnglish (US)
Pages (from-to)397-401
Number of pages5
JournalJournal of Molecular Structure
Volume410-411
DOIs
StatePublished - 1997

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adenines
nucleic acids
Adenine
Nucleic Acids
isolation
Molecules
matrices
molecules
purines
tautomers
Equilibrium constants

Keywords

  • Ab-initio calculations
  • Adenine
  • Matrix-IR spectroscopy
  • Purine
  • Tautomerism

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics

Cite this

Combined matrix-isolation FT-IR and ab-initio 6-31++G** studies on tautomeric properties of nucleic acid bases and simpler model molecules. / Houben, Linda; Schoone, Kristien; Smets, Johan; Adamowicz, Ludwik; Maes, Guido.

In: Journal of Molecular Structure, Vol. 410-411, 1997, p. 397-401.

Research output: Contribution to journalArticle

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author = "Linda Houben and Kristien Schoone and Johan Smets and Ludwik Adamowicz and Guido Maes",
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AU - Schoone, Kristien

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AU - Adamowicz, Ludwik

AU - Maes, Guido

PY - 1997

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N2 - The combined matrix isolation/ab initio 6-31++G** method is used to study the tautomeric equilibria of purine, 1-CH3-adenine, 3-CH3-adenine and N-CH3-adenine in isolated conditions. For the N9H ⇆ N7H prototropism, tautomeric equilibrium constants of 0.085, 0.090 and 0.005 are obtained for purine, 1-CH3-adenine and N-CH3-adenine, respectively. The other prototropic equilibria that are considered are the amino ⇆ imino tautomerism for which relative amounts of 5.5% for the rare amino form in 1-CH3-adenine and 0.5% for the minor imino tautomer of 3-CH3 adenine were observed, and the N9H ⇆ N3H prototropism where only 0.7% of the experimental spectrum could be accounted for by the presence of the less stable N3H form in N-CH3-adenine.

AB - The combined matrix isolation/ab initio 6-31++G** method is used to study the tautomeric equilibria of purine, 1-CH3-adenine, 3-CH3-adenine and N-CH3-adenine in isolated conditions. For the N9H ⇆ N7H prototropism, tautomeric equilibrium constants of 0.085, 0.090 and 0.005 are obtained for purine, 1-CH3-adenine and N-CH3-adenine, respectively. The other prototropic equilibria that are considered are the amino ⇆ imino tautomerism for which relative amounts of 5.5% for the rare amino form in 1-CH3-adenine and 0.5% for the minor imino tautomer of 3-CH3 adenine were observed, and the N9H ⇆ N3H prototropism where only 0.7% of the experimental spectrum could be accounted for by the presence of the less stable N3H form in N-CH3-adenine.

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