Investigation of solid state architectures in tetrazolyl tryptophol stabilized by crucial aromatic interactions and hydrogen bonding: Experimental and theoretical analysis

Ibrar A., Zaib S., Hokelek T., Simpson J., McAdam C. J., El Azab I. H., ...Daha Fazla

JOURNAL OF MOLECULAR STRUCTURE, cilt.1262, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1262
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1016/j.molstruc.2022.133079
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Anahtar Kelimeler: Noncovalent interactions, Tetrazole-indole hybrid, Crystal engineering, DFT analysis, Hydrogen bonding, ?, ? stacking, INTERMOLECULAR INTERACTIONS, HIRSHFELD SURFACES, PI-STACKING, POTENT, DERIVATIVES, ACID, FUNCTIONALIZATION, ENERGETICS, CHEMISTRY, RINGS
  • Hacettepe Üniversitesi Adresli: Evet

Özet

The present study reports the synthesis of a new nitrogen rich hybrid compound namely tetrazolyl tryp-tophol 6 achieved through a multistep synthetic approach. The structure of the target tetrazole-indole hybrid was established using FTIR, 1 H-and 13 C NMR, HRMS, and X-ray diffraction data. Investigation of solid state architectures in tetrazolyl tryptophol revealed that an intramolecular N5-H5N...N4 hydrogen bond links the 5-membered ring of the indole to the tetrazole ring. O1-H1O...N3 and N1-H1N...O1 hy-drogen bonds and n...n contacts also emerged as crucial contributors in the formation of supramolecular topology of tetrazole-indole hybrid. Numerous centroid to centroid contacts involving the aromatic rings of both the indole ring system and the tetrazole ring link adjacent molecules in an obverse face-to-face fashion. Hirshfeld surface analysis further revealed the prevailing significance of n...n and H-bonding contacts. The mechanical stability of the crystal packing through crystal voids analysis and intermolec-ular interaction energies were also calculated. Finally, DFT calculations were performed to evaluate the hydrogen bonding and n...n stacking contacts with their rationalization and characterization using MEP surfaces, QTAIM and NCIPlot analysis.(c) 2022 Elsevier B.V. All rights reserved.