1H, 13C and 15N NMR Spectral and X-ray Structural Studies of 2-Arylsulfonylamino-5-chlorobenzophenones

• Autorzy: Kolehmainen E. , Nissinen M. , Janota H. , Gawinecki R. , Ośmiałowski B.
• Języki publikacji: EN

Abstrakty

EN

Six 2-(4-R-phenylsulfonylamino)-5-chlorobenzophenones were prepared and their 1H, 13Cand 15NNMRspectra recorded and assigned. The dependence between the chemical shift of the amide proton and Hammett _ substituent constants is of the V type. Substituent effect on the chemical shift of the amide nitrogen atom was found insignificant. X-ray analysis shows that the terminal benzene rings in 2-(4-nitrophenylsulfonylamino)-5-chlorobenzophenone are located close to each other. They are not, however, parallel, dihedral angle between them being equal to 10.86 deg (MP2/6-31G**//HF/6-31G** ab initio calculations show this to be 20.44 deg). This shows that the mutual orientation of two benzene rings in the molecule of this compound is caused by the _-_ stacking. It is additionally reinforced by the intramolecular NH…O=C hydrogen bond. Except the dihedral angle between the benzene rings, X-ray determined structure of 2-(4-nitrophenylsulfonylamino)-5-chlorobenzophenone is very similar to this optimized by the ab initio calculations.

Słowa kluczowe

EN

sulfonylaminoketones; 1H and 13C NMR; X-ray diffraction; ab initio calculations; pi-pi stacking; hydrogen bonding

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2003
• Tom: Vol. 77 / nr 7
• Strony: 889--894
• Opis fizyczny: Bibliogr. 25 poz., rys.

Twórcy

autor

Kolehmainen E.

• Department of Chemistry, University of Jyväskylä, P.O. Box 35, FIN-40014 Jyväskylä, Finland

autor

Nissinen M.

• Department of Chemistry, University of Jyväskylä, P.O. Box 35, FIN-40014 Jyväskylä, Finland

autor

Janota H.

• Department of Chemistry, University of Jyväskylä, P.O. Box 35, FIN-40014 Jyväskylä, Finland

autor

Gawinecki R.

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

autor

Ośmiałowski B.

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

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