DFT Studies and Crystal Structure of Synthesized 1,3-bis(2- thiophenylmethyl)-4,5-dihydroimidazolidinium hexafluorophosphate Salt

Authors : Senem Akkoc, Sevim Türktekin Çelikesir, Yetkin Gök, Sevtap Çağlar Yavuz, Mehmet Akkurt, Namık Özdemir

Pages : 45-58

Doi:10.18596/jotcsa.67666

View : 13 | Download : 4

Publication Date : 2017-01-09

Article Type : Research Paper

Abstract :Synthesized compound 5 , insert ignore into journalissuearticles values(C 13 H 15 N 2 S 2 );[PF 6 ], was fully characterized with X-ray diffraction method. In this compound, the asymmetric unit contains a 1,3-insert ignore into journalissuearticles values(2-thiophenylmethyl);-4,5-dihydroimidazolidinium cation and a hexafluorophosphate anion. Due to an 180° rotation about the thiophene-CH 2 bonds, the thiophene rings in the cation are disordered [site-occupancy factors = 0.903insert ignore into journalissuearticles values(4);/0.097insert ignore into journalissuearticles values(4); and 0.837insert ignore into journalissuearticles values(5);/0.163insert ignore into journalissuearticles values(5);, respectively]. The short C—N bond lengths [1.303insert ignore into journalissuearticles values(4); and 1.287insert ignore into journalissuearticles values(4); Å] in the imidazolidine ring display partial electron delocalization within the N—C—N fragment. Anion and cations are connected through intermolecular C—H...F hydrogen bonds and three p-p stacking interactions [centroid-centroid distances = 3.890insert ignore into journalissuearticles values(3);, 3.852insert ignore into journalissuearticles values(5); and 3.816insert ignore into journalissuearticles values(7); Å] between the thiophene rings of the adjacent cations, forming layers parallel to insert ignore into journalissuearticles values(011);. Furthermore, we studied theoretical studies of this compound, too. Geometry optimization was carried out in gas phase by Density Functional Theory insert ignore into journalissuearticles values(DFT); method with B3LYP applying 6-311++G ** basis set. The obtained results from experimental and theoretical structural properties of compound 5 had been compared to each other. 
Keywords : Imidazolidinium salt, synthesis, crystal structure, DFT, CH F hydrogen bonds, stacking interactions