ReviewMolecules (Basel, Switzerland)2023
On Prototropy and Bond Length Alternation in Neutral and Ionized Pyrimidine Bases and Their Model Azines in Vacuo.
Review in Molecules (Basel, Switzerland), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed, 7 citations in OpenAlex.
- Linking Enol-Keto Tautomerization Ratios in β‑Diketones to Their Physical Properties Using Computational Quantum Chemistry.ACS omega · 2026Article
- Occurrence, Properties, Applications and Analytics of Cytosine and Its Derivatives.Molecules (Basel, Switzerland) · 2025Review
- Quantum Chemical Studies on the Prototropic and Acid/Base Equilibria for 2-Aminopyrrole in Vacuo-Role of CH Tautomers in the Design of Strong Brønsted Imino N-Bases.Molecules (Basel, Switzerland) · 2025Article
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1 author at 1 institution in 1 country.
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Abstract
In this review, the complete tautomeric equilibria are derived for disubstituted pyrimidine nucleic acid bases starting from phenol, aniline, and their model compounds-monosubstituted aromatic azines. The differences in tautomeric preferences for isolated (gaseous) neutral pyrimidine bases and their model compounds are discussed in light of different functional groups, their positions within the six-membered ring, electronic effects, and intramolecular interactions. For the discussion of tautomeric preferences and for the analysis of internal effects, recent quantum-chemical results are taken into account and compared to some experimental ones. For each possible tautomer-rotamer of the title compounds, the bond length alternation, measured by means of the harmonic oscillator model of electron delocalization (HOMED) index, is examined. Significant HOMED similarities exist for mono- and disubstituted derivatives. The lack of parallelism between the geometric (HOMED) and energetic (Δ
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