Citation: MUHAMMAD Naeem Ahmeda, KHAWAJA Ansar Yasina, TARIQ Mahmood, FATIMA Wasim, MUHAMMAD Haleem Khan, M. NAWAZ Tahir, SAFEENA Zafar, SHAISTA Anjum. Synthesis and Structural Investigations of New 4-Hexyl-1-(4-nitrophenyl)-1-H-1,2,3-triazole: An Experimental and Theoretical Insight[J]. Chinese Journal of Structural Chemistry, ;2015, 34(12): 1830-1840. doi: 10.14102/j.cnki.0254-5861.2011-0864 shu

Synthesis and Structural Investigations of New 4-Hexyl-1-(4-nitrophenyl)-1-H-1,2,3-triazole: An Experimental and Theoretical Insight

a.
a. Department of Chemistry, The University of Azad Jammu and Kashmir, Muzaffarabad 13100, Pakistan;
b.
b. Department of Chemistry, COMSATS Institute of Information Technology, University Road, Tobe Camp, 22060 Abbottabad, Pakistan;
c.
c. Department of Chemistry, Women University Bagh Azad Kashmir;
d.
d. Department of Physics, University of Sargodha, Sargodha, Pakistan

Received Date: 23 August 2015
Available Online: 3 November 2015
Fund Project: This work was supported by the Higher Education Commision (HEC) (HEC)

The title compound, 4-hexyl-1-(4-nitrophenyl)-1-H-1,2,3-triazole (C₁₄H₁₈N₄O₂), was synthesized using one-pot strategy via click reaction and the structure was characterized mainly by single-crystal X-ray diffraction, NMR, FT-IR and MS. C₁₄H₁₈N₄O₂ was crystallized from an EtOH/EtOAc solution in triclinic system, space group P1, with a=5.3679(3), b=7.5499(5), c=17.5534(11) Å, α=92.360(4), β=90.359(4), γ=98.864(4)°, V (Å³)=702.24(8), Z=2, crystal size (mm)=0.42×0.26×0.18, R_int=0.096. Packing diagram indicates that there is dimeric interaction between two units via N(3)…H(6). The crystal structure of the title compound (1) is stabilized by intermolecular interactions. In addition, X-ray analysis also reveals C-H…π and π-π interactions in the molecule. Theoretical investigations were performed by using Gaussian 09 software at the B3LYP/6-31G (d,p) level of density finctional theory (DFT) to compare the theoretical results with the experimental and to probe structural properties. The molecular electrostatic potential (MEP) mapped over the entire stabilized geometry of the molecule indicated their chemical reactivities. Furthermore, frontier molecular orbital (electronic properties) was computed at the same level of DFT as used for energy minima structure.
- click chemistry,
- disubstituted triazole,
- X-ray,
- DFT,
- MEP,
- frontier molecular orbital
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