Predominance of (E)-1,2-Di(pyridin-2-yl)ethene-1,2-diol over 2-Hydroxy-1,2-di(pyridin-2-yl)ethanone in Solution

• Autorzy: Gawinecki R. , Ośmiałowski B. , Kolehmainen E.
• Języki publikacji: EN

Abstrakty

EN

1H, 13C and 15N NMR spectra, supported by the GIAO/DFT calculated (B3LYP/6- 311G//RHF/3-21G) 13C and 15N (B3LYP/6-31++G**//RHF/3-21G) NMR chemical shifts, show that (E)-1,2-di(pyridin-2-yl)ethene-1,2-diol (OO3) is the only tautomer present in chloroform solution. MP2/6-31G**//RHF/6-31G** and MP2/6-31G** ab initio calculations confirm that this perfectly planar form is really more stable than 2-hydroxy-1,2-di(pyridin-2-yl)ethanone (OK1, OK2 and OK3) and other isomeric dimers of pyridine-2-carboxaldehyde. The strong intramolecular hydrogen bonds are responsible for high stability of (E)-1,2-di(pyridin-2-yl)ethene-1,2-diol (the conjugation in the molecule is of minor importance).

Słowa kluczowe

EN

enols; tautomerism; ab initio calculations; NMR spectroscopy; structure elucidation

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2003
• Tom: Vol. 77 / nr 11
• Strony: 1411--1417
• Opis fizyczny: Bibliogr. 29 poz., rys.

Twórcy

autor

Gawinecki R.

• Department of Chemistry, Technical and Agricultural University, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland

autor

Ośmiałowski B.

• Department of Chemistry, Technical and Agricultural University, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland

autor

Kolehmainen E.

• Department of Chemistry, University of Jyväskylä, P.O. Box 35, FIN-40351 Jyväskylä, Finland

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