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
1. [1]
  Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-. doi: 10.3866/PKU.WHXB202312010
2. [2]
  Tsegaye Tadesse Tsega , Jiantao Zai , Chin Wei Lai , Xin-Hao Li , Xuefeng Qian . Earth-abundant CuFeS2 nanocrystals@graphite felt electrode for high performance aqueous polysulfide/iodide redox flow batteries. Chinese Journal of Structural Chemistry, 2024, 43(1): 100192-100192. doi: 10.1016/j.cjsc.2023.100192
3. [3]
  Chunyan Yang , Qiuyu Rong , Fengyin Shi , Menghan Cao , Guie Li , Yanjun Xin , Wen Zhang , Guangshan Zhang . Rationally designed S-scheme heterojunction of BiOCl/g-C₃N₄ for photodegradation of sulfamerazine: Mechanism insights, degradation pathways and DFT calculation. Chinese Chemical Letters, 2024, 35(12): 109767-. doi: 10.1016/j.cclet.2024.109767
4. [4]
  Run-Han Li , Tian-Yi Dang , Wei Guan , Jiang Liu , Ya-Qian Lan , Zhong-Min Su . Evolution exploration and structure prediction of Keggin-type group IVB metal-oxo clusters. Chinese Chemical Letters, 2024, 35(5): 108805-. doi: 10.1016/j.cclet.2023.108805
5. [5]
  Chaozheng He , Jia Wang , Ling Fu , Wei Wei . Nitric oxide assists nitrogen reduction reaction on 2D MBene: A theoretical study. Chinese Chemical Letters, 2024, 35(5): 109037-. doi: 10.1016/j.cclet.2023.109037
6. [6]
  Ting-Ting Huang , Jin-Fa Chen , Juan Liu , Tai-Bao Wei , Hong Yao , Bingbing Shi , Qi Lin . A novel fused bi-macrocyclic host for sensitive detection of Cr₂O₇²⁻ based on enrichment effect. Chinese Chemical Letters, 2024, 35(7): 109281-. doi: 10.1016/j.cclet.2023.109281
7. [7]
  Sanmei Wang , Yong Zhou , Hengxin Fang , Chunyang Nie , Chang Q Sun , Biao Wang . Constant-potential simulation of electrocatalytic N₂ reduction over atomic metal-N-graphene catalysts. Chinese Chemical Letters, 2025, 36(3): 110476-. doi: 10.1016/j.cclet.2024.110476
8. [8]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
9. [9]
  Chen Chen , Jinzhou Zheng , Chaoqin Chu , Qinkun Xiao , Chaozheng He , Xi Fu . An effective method for generating crystal structures based on the variational autoencoder and the diffusion model. Chinese Chemical Letters, 2025, 36(4): 109739-. doi: 10.1016/j.cclet.2024.109739
10. [10]
  Hongwei Ma , Fang Zhang , Hui Ai , Niu Zhang , Shaochun Peng , Hui Li . Integrated Crystallographic Teaching with X-ray,TEM and STM. University Chemistry, 2024, 39(3): 5-17. doi: 10.3866/PKU.DXHX202308107
11. [11]
  Jingqi Ma , Huangjie Lu , Junpu Yang , Liangwei Yang , Jian-Qiang Wang , Xianlong Du , Jian Lin . Rational design and synthesis of a uranyl-organic hybrid for X-ray scintillation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100275-100275. doi: 10.1016/j.cjsc.2024.100275
12. [12]
  Xin Dong , Jing Liang , Zhijin Xu , Huajie Wu , Lei Wang , Shihai You , Junhua Luo , Lina Li . Exploring centimeter-sized crystals of bismuth-iodide perovskite toward highly sensitive X-ray detection. Chinese Chemical Letters, 2024, 35(6): 108708-. doi: 10.1016/j.cclet.2023.108708
13. [13]
  Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
14. [14]
  Hong-Jin Liao , Zhu Zhuo , Qing Li , Yoshihito Shiota , Jonathan P. Hill , Katsuhiko Ariga , Zi-Xiu Lu , Lu-Yao Liu , Zi-Ang Nan , Wei Wang , You-Gui Huang . A new class of crystalline X-ray induced photochromic materials assembled from anion-directed folding of a flexible cation. Chinese Chemical Letters, 2024, 35(8): 109052-. doi: 10.1016/j.cclet.2023.109052
15. [15]
  Xuying Yu , Jiarong Mi , Yulan Han , Cai Sun , Mingsheng Wang , Guocong Guo . A stable radiochromic semiconductive viologen-based metal–organic framework for dual-mode direct X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109233-. doi: 10.1016/j.cclet.2023.109233
16. [16]
  Xin Dong , Tianqi Chen , Jing Liang , Lei Wang , Huajie Wu , Zhijin Xu , Junhua Luo , Li-Na Li . Structure design of lead-free chiral-polar perovskites for sensitive self-powered X-ray detection. Chinese Journal of Structural Chemistry, 2024, 43(6): 100256-100256. doi: 10.1016/j.cjsc.2024.100256
17. [17]
  Yan-Jiang Li , Shu-Lei Chou , Yao Xiao . Detecting dynamic structural evolution based on in-situ high-energy X-ray diffraction technology for sodium layered oxide cathodes. Chinese Chemical Letters, 2025, 36(2): 110389-. doi: 10.1016/j.cclet.2024.110389
18. [18]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
19. [19]
  Bingwei Wang , Yihong Ding , Xiao Tian . Benchmarking model chemistry composite calculations for vertical ionization potential of molecular systems. Chinese Chemical Letters, 2025, 36(2): 109721-. doi: 10.1016/j.cclet.2024.109721
20. [20]
  Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(780)
HTML views(9)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return