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Technical Issues
2/2017 pp. 23-28

Tautomeria prototropowa związków organicznych


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Abstract

Tautomerism is a phenomenon of existing of structural isomers of the compound, which are in balance with each other. The most common type of tautomerism associated with migration of hydrogen and redistribution of electron density is prototropic tautomerism. Tautomers generally differ significantly in physicochemical properties and reactivity. Researches on tautomeric balance were the subject of broad interest to biochemists. Several compounds exhibiting biological activity may in fact occur in more than one tautomeric form. It is recognized that tautomers plays an important role in the interaction with DNA molecules, processes transporting living matter, or the appearance of spontaneous mutations. Therefore, for many years the researches on this phenomenon have been conducted, both experimental and theoretical.

Key words

tautomerism of heterocyclic compounds, methods of tautomerism research

References

1. Ebead, Y., Wróblewska, A., Krzymiński, K., Rak, J., Błażejowski, J., NMR and DFT investigations of the substituent and solvent effect on amino-imino tautomerism in acridin-9-amines substitued at the exocyclic nitrogen atom, Journal of Physical Organic Chemistry, 2005, 18, pp. 870-879.

2. Fijałkow, J.J., Żytomirski, A.N., Tarasenko, J.A., Chemia fizyczna roztworów niewodnych, PWN, Warszawa, 1983.

3. Katritzky, A.R., Ambler, A.P., Physical Methods in Heterocyclic Chemistry, Academic Press, New York, 1963.

4. Katritzky, A.R., Lagowski, J.M., Prototropic Tautomerism of Heteroaromatic Compounds: I. General Discussion and Methods of Study, W: Advanced in Heterocyclic Chemistry, 1963, Vol. 1. pp. 312-338.

5. March, J., Chemia organiczna. Reakcje, mechanizmy, budowa, WNT, Warszawa, 1975.

6. Nesmeyanov, W., Theoretical Principles of Organic Chemistry (English Translation), (red. Reutov O.A.), MIR Publishers, Moscow, 1970.

7. Wheland, G.W., Advanced Organic Chemistry, 3 Ed. Wiley, New York, 1960, 663-730.