Synthesis, X-Ray crystallography and HF/DFT analysis of N(diethylcarbamothioyl) furan-2-carboxamide, analyzed by experimental and theoretical methods

Saeed A., Ashraf S., Shabir G., HÖKELEK T., Floerke U., Mukhtar A., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1268, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1268
  • Publication Date: 2022
  • Doi Number: 10.1016/j.molstruc.2022.133721
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Keywords: Crystal structure, Hirshfeld surface analysis, Thiourea, Natural Bond Analysis, Hydrogen bond, INTERMOLECULAR INTERACTIONS, CRYSTAL-STRUCTURE, QUANTITATIVE-ANALYSIS, THIOUREAS, DERIVATIVES, ADSORPTION, DFT
  • Hacettepe University Affiliated: Yes


Reaction of freshly prepared furanoyl isothiocyanate ( 2 ) with diethyl amine afforded N- (diethylcarbamothioyl)furan-2-carboxamide ( 3 ) in an excellent yield and purity. The furanoyl isoth-iocyanate ( 2 ) was, in turn, obtained by a reaction between furanoyl chloride ( 1 ) with potassium thiocyanate. The structure of 3 was deduced by spectroscopic data and elemental analysis and cor-roborated by single crystal X-ray crystallography. The crystal data indicated that the furan ring is almost coplanar with the aminocarbamothioyl moiety in 3 , facilitating an intra-molecular hydrogen bond between oxygen of the furan ring and NH of thiourea group. Detailed analysis of intermolecular interactions in the crystal was performed by applying the Hirshfeld surface method, indicating that crystal packing is facilitated (up to 55%) by an intermolecular hydrogen bonding between NH on one molecule and the carbonyl oxygen on the other. Finally, quantum chemical analysis of 3 was conducted using ab initio (6-311 + G **) and density functional (B3LYP/6-311 + G **) models for determination of elec-trochemical properties of the title compound. Both the Hartree Fock (HF) and density functional theory (DFT) predicted identical 3D structure for 3, which matches closely with the X-Ray Crystal structure. The NBO analyses, molecular electrostatic potential (MEP) and total density of states (DOS) are accomplished along with other the electrochemical properties of 3 including ionization potential ( I ), electron affinity ( A ), chemical hardness (eta), electronic chemical potential (mu) and electrophilicity (omega). (C) 2022 Elsevier B.V. All rights reserved.