Vibrational spectral analysis, XRD-structure, computation, exo⇔endo isomerization and non-linear optical crystal of 5-((5-chloro-1 H-indol-2-yl)methylene)-1,3-diethyl-2-thioxodihy-dropyrimidine-4,6 (1 H,5 H)-dione

Mezna Saleh Altowyan; Assem Barakat; Abdullah Mohammed Al-Majid; Hazem A Ghabbour; Abdelkader Zarrouk; Ismail Warad

doi:10.1186/s13065-019-0524-8

Vibrational spectral analysis, XRD-structure, computation, exo⇔endo isomerization and non-linear optical crystal of 5-((5-chloro-1 H-indol-2-yl)methylene)-1,3-diethyl-2-thioxodihy-dropyrimidine-4,6 (1 H,5 H)-dione

BMC Chem. 2019 Feb 2;13(1):11. doi: 10.1186/s13065-019-0524-8. eCollection 2019 Dec.

Authors

Mezna Saleh Altowyan¹, Assem Barakat^{2

3}, Abdullah Mohammed Al-Majid², Hazem A Ghabbour^{4

5}, Abdelkader Zarrouk⁶, Ismail Warad⁷

Affiliations

¹ 1Department of Chemistry, College of Science, Princess Nourah Bint Abdulrahman University, Riyadh, Saudi Arabia.
² 2Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh, 11451 Saudi Arabia.
³ 3Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria, 21321 Egypt.
⁴ 4Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh, 11451 Saudi Arabia.
⁵ 5Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura, 35516 Egypt.
⁶ 6Laboratory of Materials, Nanotechnology and Environment, Faculty of Science, Mohammed V University, 4Av. IbnBattuta, B.P. 1014 Rabat, Morocco.
⁷ 7Department of Chemistry, Science College, An-Najah National University, P.O. Box 7, Nablus, Palestine.

Abstract

This work deals with the synthesis and characterization of the novel 5-((5-chloro-1H-indol-2-yl)methylene)-1,3-diethyl-2-thioxodihydro-pyrimidine-4,6(1H,5H)-dione π-bridge (D-A-D) donor-acceptor-donor compound. Its exo-isomer structure has been proven by XRD-single-crystal analysis for the first time. The IR, UV-Vis., MS, CHN-, ¹H and ¹³C NMR analysis were also carried out. The DFT-optimized structural-parameters were matched with the XRD-crystallographic data. The experimental-XRD-interactions in the lattice were compared to the computed Hirshfeld analysis (HSA), MEP map and Mulliken charge population. The DFT/6-311G(d) calculations like IR/B3LYP, TD-SCF, HOMO-LUMO, GRD and GIAO-NMR have been compared to their corresponding experimental parameters. Non-linear optical (NLO) crystal theoretical-analysis was carried out then compared to urea reference. The compound thermal activity was evaluated in an open-atmosphere by TG/DTG analysis.

Keywords: Condensation; Exo–endo isomer; Thiobarbituric acid; XRD.