Synthesis, crystal and molecular structure, and characterization of 2-((2-aminopyridin-3-yl)methylene)-N-ethylhydrazinecarbothioamide using spectroscopic (1H and 13C NMR, FT-IR, FT-Raman, UV–Vis) and DFT methods and evaluation of its anticancer activity

• Published in: Journal of molecular structure Vol. 1184; pp. 405 - 417
• Main Authors: Ramaiah, K., Srishailam, K., Laxma Reddy, K., Reddy, B. Venkatram, Ramana Rao, G.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.05.2019
• Subjects: Anticancer activity; Crystal structure; DFT; Hydrazinecarbothioamide; NMR; UV–Vis spectra; Vibrational spectra; NMR; DFT; UV–Vis spectra; Anticancer activity; Hydrazinecarbothioamide; Vibrational spectra; Crystal structure
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2019.02.060

2-((2-aminopyridin-3-yl)methylene)-N-ethylhydrazinecarbothioamide was synthesized. It was characterized by making elemental analysis, assisted by experimental 1H NMR, 13C NMR, FT- Raman (4000-50 cm−1), FT-IR (4000-400 cm−1), and UV–Vis (200–400 nm) spectra and evaluating its anticancer activity, for human carcinoma cell lines HeLa (cervical), IMR-32 (neuroblastoma) and A549 (lung). Crystal and molecular structure of the molecule was determined by means of X-ray diffractometry, which showed that it belongs to triclinic crystal system, with space group P-1, having two molecules per unit cell (Z = 2). The parameters of the unit cell are a = 6.0960 (6) Å, b = 7.4119 (8) Å, c = 11.9959 (13) Å, α = 82.1695 (4)°, β = 81.6407 (4)°, γ = 88.3283 (4)° at 100 K. Quantum chemical computations were made using density functional theory (DFT), B3LYP functional and 6–311++G (d,p) basis set in order to determine optimized structure parameters, general valence force field, harmonic vibrational frequencies, potential energy distribution, infrared and Raman intensities, NLO properties, frontier molecular orbital parameters and NBO characteristics. Its time-dependent variant (TD-DFT) was used to calculate the oscillator strengths and absorption maxima (λmax) in DMSO‑d6 as a solvent, of various electronic transitions. There was a good agreement between the theoretical and experimental parameters such as molecular structure parameters, IR, Raman and UV–Vis spectra. The rms error between measured and estimated vibrational frequencies was 6.9 cm−1. The calculations showed that the molecule under investigation was good for NLO applications, which was supported by NBO analysis. ▪ •Crystal and molecular structure of newly synthesized material (APTA) have been determined.•FT-IR, FT-Raman, 1H NMR, 13C NMR, UV–Vis spectra have been measured.•Unambiguous vibrational assignments of all vibrational fundamentals, NMR signals and UV–Vis spectra are made for the first time.•Existence of intra-molecular hydrogen bond is proved both experimentally and theoretically, exhibits NLO and anticancer properties.