Predominance of Amino-Sulfonyl Hydrogen Bonding in (Z)-2-Benzene-sulfonyl-1-phenyl-2-(phenylhydrazono)ethanones in Crystals adn in Solution: An Experimental NMR and X-ray Crystallographic and Theoretical Ab initio and DFT/GIAO Studies

• Autorzy: Kolehmainen E. , Zakrzewski A. , Zakrzewska A. , Nissinen M. , Ośmiałowski B. , Gawinecki R.
• Języki publikacji: EN

Abstrakty

EN

1H, 13C, and 15N NMR spectra show that (Z)-2-benzenesulfonyl-1-phenyl-2-(phenylhydrazono) ethanone is the only tautomeric form detected in chloroform solution. Substituent in the phenylhydrazone moiety does not affect this tautomeric preference. Ab initio calculations show that (Z)-2-benzenesulfonyl-1-phenyl-2-(phenylhydrazono)ethanone is really favoured over its proton transfer products in chloroform solution. This shows that N-H...OS(O) interaction is much stronger than the hydrogen bonds in other tautomeric forms. The (Z)-2-benzene-sulfonyl-1-phenyl-2-(phenylhydrazono)ethanone tautomer was also detected in the crystal state.

Słowa kluczowe

EN

tautomers; monohydrazones of diketosulfones; hydrogen bonding; X-ray diffraction; NMR; DFT and ab initio calculations

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2003
• Tom: Vol. 77 / nr 1
• Strony: 31--45
• Opis fizyczny: Bibliogr. 32 poz., rys.

Twórcy

autor

Kolehmainen E.

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

autor

Zakrzewski A.

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

autor

Zakrzewska A.

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

autor

Nissinen M.

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

autor

Ośmiałowski B.

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

autor

Gawinecki R.

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