Adamantylazoles. 5. The molecular structure of 1-(1-adamantyl)pyrazoles

• Published in: Journal of heterocyclic chemistry Vol. 23; no. 4; pp. 1045 - 1050
• Main Authors: Cabildo, P., Claramunt, R. M., Sanz, D., Foces-Foces, M. C., Cano, F. Hernández, Fayet, J. P., Vertut, M. C., Elguero, J.
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley-Blackwell 01-07-1986; Wiley‐Blackwell
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.5570230416

The crystal structures of 1‐(1‐adamantyl)‐3,5‐dimethylpyrazole 1 and 1‐(1‐adamantyl)‐3,4,5‐trimethylpyrazole 2 were studied by X‐ray analysis. The space groups and cell parameters are: 1, Cc, 13.4452(4), 14.9407(4), 7.1119(2) Å, 90, 111.944(2), 90°, with Z = 4. 2, P21/c, 6.7466(1), 21.2565(7), 10.1462(2) Å, 90, 106.368(2), 90°, with Z = 4. The final disagreement factors were 0.069 and 0.061, for 721 [2σ(I)] and 1950 [2σ(I)] observed reflexions, respectively. Compound 1 presents the adamantyl residue disordered between the two usual conformations. The experimental dipole moments and the carbon‐13 chemical shifts (both in hexadeuteriodi‐methylsulfoxide and in the solid state) were measured and discussed in connection with the structure of these compounds.