Crystallographic and NMR analysis of 9-phenylthiophenanthrene and 9-tert-butylthiophenanthrene

Abstract

The crystal structures of 9-phenylthiophenanthrene (C 20 H 14 S) and 9-tert-butylthiophenanthrene (C 18 H 18 S) were determined at 193 K. The former crystallizes in orthorhombic space group P2 1 2 1 2 1 (No. 19) with cell dimensions a = 5.602( 2), b = 9.247(3), and c = 27.508(12) Å and the latter in orthorhombic space group Pbcn (No. 60) with cell parameters a = 21.335(4), b = 7.540(2), and c = 18.197(4) Å. In both compounds the substituents at sulfur are nearly perpendicular to the phenanthrene plane. NMR spectra of the compounds were recorded in CDCl 3 . The 1 H NMR spectral parameters were analyzed in detail by using an iterative spectral analysis program. The 13 C{ 1 H} resonances were fully assigned with the aid of two-dimensional heteronuclear chemical shift correlation spectra. On the basis of the NOE difference spectra the orientation of the side chain was concluded to be similar to that in the solid state.

Di-9-anthryl disulfide at 193 K

“…The crystal structure determination of 9-dianthryl disul®de, (I), is part of our investigation dealing with polyaromatic sul®des (Kansikas & Sipila È , 1997Sipila È & Hase, 1997;Sipila È et al, 1999). A simple preparation method for (I) has been reported by Majumdar et al (1986), who synthesized the product in 90% yield by re¯uxing anthrone, P 2 S 5 and anhydrous pyridine for 5 h. The compound used in this X-ray analysis was obtained as a side product when testing preparation methods for 9-anthracenethiol.…”

Two 9-alkylthiophenanthrenes at 193 K (alkyl = dodecyl and tetradecyl)

“…We have studied the structures of 9-phenylthiophenanthrene (VI) and 9-tert-butylthiophenanthrene (VII; Sipila È et al, 1999). In these compounds the substituents deviate from the phenanthrene planes.…”