The crystal and molecular structure of cyclic thioamide beta-dikotone derivatives. Intramolecular H-bonding and the problem of quasiaromaticity

• Autorzy: Anulewicz R. , Krygowski T.M. , Jagodziński T.
• Języki publikacji: EN

Abstrakty

EN

Crystal and molecular structures of the 2,6-dioxocyclohexanethiocarboxanilide (I), 4,4-dimethyl-2,6-dioxocyclohexanethiocarboxanilide (II) and 1,3-indandione-2- thiocarboxanilide (III) have been determined by use of X-ray diffraction technique on a Kuma-diffractometer. Crystal data for compound (I): C13H13N1O2S1, M-r=247.32, monoclinic, C2/c, a=22.704(5)A, b=7.312(1)A, c=17.192(3)A, beta=123.07(3), Z=8, R=0.0597 for 2181 reflections. Compound (II): C15H17N1O2S1, M-r=275.36, triclinic, P-1, a=10.748(1)A, b=9.223(2)A, c=7.346(2)A, alpha=91.21(3), beta=100.36(3), gamma=76.01(3), Z=2, R=0.0733 for 2485 reflections. Compound (III): C16H11N1O2S1, M-r=281.12, triclinic, P-1, a=6.945(3)A, B=8.786(1)A, c=12.435(3)A, alpha=86.97(3), beta=73.78(3), gamma=66.74(3), Z=2,R=0,0696 for 2361 reflections. Of the two potentially H-bonding systems of each of the title compounds one that with OH...S, is stronger and this resilts in a stronger pi-electron delocalization. This is quantitatively measured by HOMA index, which is by ca. 0.3 units larger than for the other H-bonding system, the one with the NH...O bridge.

Słowa kluczowe

EN

X-ray diffraction; molecular geometry; cross-conjugates system; H-bonding; quasiaromaticity

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 1998
• Tom: Vol. 72, nr 2
• Strony: 439--448
• Opis fizyczny: Bibliogr. 15 poz., tab.

Twórcy

autor

Anulewicz R.

autor

Krygowski T.M.

autor

Jagodziński T.

• Department of Chemistry University of Warsaw ul. Pasteura 1 02-093 Warsaw Poland