Geometric and energetic consequences of prototropy for adenine and its structural models – a review
| العنوان: | Geometric and energetic consequences of prototropy for adenine and its structural models – a review |
|---|---|
| المؤلفون: | Beata Kamińska, Ewa D. Raczyńska, Mariusz Makowski, Małgorzata Hallmann |
| المصدر: | RSC Advances. 5:36587-36604 |
| بيانات النشر: | Royal Society of Chemistry (RSC), 2015. |
| سنة النشر: | 2015 |
| مصطلحات موضوعية: | Purine, Proton, Stereochemistry, General Chemical Engineering, Heteroatom, General Chemistry, Tautomer, Amidine, chemistry.chemical_compound, Delocalized electron, chemistry, Computational chemistry, Atom, Imidazole |
| الوصف: | Heterocycles containing one or more amidine moieties {–NH–C(R) N–} such as adenine and its building blocks, imidazole, 4-aminopyrimidine, and purine, are excellent examples of tautomeric systems for which changes of position(s) of labile proton(s) cause parallel changes of geometric and energetic parameters for prototropic tautomers. One-electron oxidation has a slight effect on this relationship. The amino-imine conversions within the amidine group(s) are favored. Well delocalized (aromatic) tautomers, containing labile proton(s) at heteroatom(s), are major, minor, or rare forms. Non-aromatic tautomers with a labile proton at the C atom can be considered as very rare isomers. Dramatic changes take place for reduced heterocycles. Electron delocalization is not the main factor that dictates tautomeric preferences. The HOMED/ΔE relationship seems to be more complex. The enamino-imine conversions predominate and some very rare forms have the lowest energies. This clearly shows the importance of very rare tautomers, often neglected in proton-transfer, electron-transfer, and ion–radical reactions. |
| تدمد: | 2046-2069 |
| DOI: | 10.1039/c4ra17280a |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::6e0eec52487239d757be860c732fb803 https://doi.org/10.1039/c4ra17280a |
| Rights: | OPEN |
| رقم الانضمام: | edsair.doi...........6e0eec52487239d757be860c732fb803 |
| قاعدة البيانات: | OpenAIRE |
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