4,5-, 3,6-, and 3,4,5,6-tert-Butylsulfanylphthalonitriles: synthesis and comparative structural and spectroscopic analyses

Abstract

Three tert-butylsulfanylphthalonitriles have been prepared with optimized synthetic procedures. Their comparative structural analyses have been completed, with a focus on IR and NMR spectroscopy and refined X-ray structural data. Miscellaneous parameters such as UV absorption, melting points, and related polarity of the compounds are summarized.

Molecular structure, spectroscopic and DFT computational studies on 4,5-bis(tert-butylsulfanyl)phthalonitrile

“…This angle has been calculated at 1.64°for the B3LYP/6-311++G(d,p) level. However, the second butylsulfanyl group is nearly perpendicular to the phenyl ring with an angle of 80.90 (7)°between the plane formed by C6, S2, and C13 and the plane of the phenyl ring [24]. This dihedral angle has been calculated at 77.59°for B3LYP.…”

“…The most notable discrepancy occurs in the orientation of the butylsulfanyl groups in the compound. In the compound, one of the butylsulfanyl groups is nearly situated in the same plane as the phenyl ring with an angle of 16.62 (7)°between the mean plane of the phenyl ring and the plane that goes through atoms C5, S1, and C9 [24]. This angle has been calculated at 1.64°for the B3LYP/6-311++G(d,p) level.…”

“…The atomic numbering scheme for the title crystal [24] and the theoretical geometric structure of the title compound are shown in Fig. 1a and b.…”

“…The crystal structure of the title compound is triclinic and space group is P-1. The crystal structure parameters of the compound are a = 9.395 (4) Å, b = 9.577 (4) Å, c = 11.080 (5) Å, a = 80.79 (1)°, b = 75.76 (1)°, c = 63.31 (1)°and V = 861.9 (6) Å 3 [24].…”

“…In previous publication, the X-ray, IR, 1 H and 13 C NMR of 4,5-bis(tert-butylsulfanyl)phthalonitrile were reported [24]. In despite of its importance, mentioned above, there is no theoretical calculation on 4,5-bis(tert-butylsulfanyl)phthalonitrile published.…”