PREPARATION, CRYSTAL AND MOLECULAR-STRUCTURE AND PROPERTIES OF 5,5'-BIS-(1,3-DITHIOL-2-YLIDENE) [BICYCLOPENTA-1,3-DIEN-1-YL]-2,2',3,3'-TETRACARBONITRILE

• Published in: J. Chem. Soc., Perkin Trans. 2 no. 3; pp. 373 - 376
• Main Authors: NALEWAJEK, D, LULY, MH, KAPLAN, ML, CHURCHILL, MR, ZILLER, J, SCHABER, PM
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 1993; Royal Society of Chemistry
• Subjects: Chemistry; Chemistry, Organic; Chemistry, Physical; Condensed matter: structure, mechanical and thermal properties; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Organic compounds; Physical Sciences; Physics; Preparations and properties; Science & Technology; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; ANION; COMPLEXES; Five membered ring; Sulfur heterocycle; Nitrile; Molecular structure; Recrystallization; Conjugated dienic compound; Experimental study; X ray diffraction; Organic compounds; Crystalline structure
• ISSN: 0300-9580; 2050-8239; 1364-5471
• DOI: 10.1039/p29930000373

The synthesis and properties of 2-(3,4-dicyanocyclopenta-2,4-dienylidene)-1,3-dithiole 2 have been previously reported. NMR spectral data of that compound imply a large contribution of the dipolar form to its electronic structure. Two-solvent diffusion recrystallization, in the presence of O2, yields the title compound 3, the crystal structure of which is reported here. This appears to be the first crystal structure of a compound containing the dicyanocyclopentadiene moiety. The space group is P1- and the lattice parameters are a = 8.3617(19), b = 11.1196(23), c = 12.8159(20) angstrom, alpha = 96.587(15)-degrees, beta = 103.103(15)-degrees, gamma = 109.917(16)-degrees and V = 1066.9(4) angstrom3 for Z = 2. We also discuss a plausible mechanism for the formation of compound 3, and its spectral properties.