Synthesis, characterization, and crystal structures of N, N'-bis-(2-di-alkyl-amino-phen-yl)thio-ureas

Kyounghoon Lee

doi:10.1107/S2056989022012245

Synthesis, characterization, and crystal structures of N, N'-bis-(2-di-alkyl-amino-phen-yl)thio-ureas

Acta Crystallogr E Crystallogr Commun. 2023 Jan 6;79(Pt 2):60-64. doi: 10.1107/S2056989022012245. eCollection 2023 Jan 1.

Author

Kyounghoon Lee¹

Affiliation

¹ Department of Chemical Education and Research Institute of Natural Sciences, Gyeongsang National University, Gyeongsangnam-do 52828, Republic of Korea.

Abstract

N,N'-Bis[2-(di-methyl-amino)-phen-yl]thio-urea, C₁₇H₂₂N₄S (1), and N,N'-bis-[2-(di-ethyl-amino)-phen-yl]thio-urea, C₂₁H₃₀N₄S (2), were prepared by the treatment of 1,1'-thio-carbonyl-diimidazole and 2 equivalents of 2-amino-N,N'-di-alkyl-aniline. Both compounds exhibit intra-molecular hydrogen bonds between the N-H(thio-urea) and NR ₂ (R = Me, Et) groups. The other N-H bonds face the sulfur atoms of S=C bonds in an adjacent mol-ecule, which forms an inter-molecular inter-action in the packed structure. The structural details match the spectroscopic data acquired from NMR and IR spectroscopy.

Keywords: aryl-substituted thiourea; crystal structure; hydrogen bond.

Grants and funding

Funding for this research was provided by: National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (2021R1G1A1093332 and 2022R1F1A1064158).