Journal of Guangxi Normal University(Natural Science Edition) ›› 2013, Vol. 31 ›› Issue (1): 57-61.

Previous Articles     Next Articles

Synthesis,Crystal Structure and Spectroscopic Studies of 2-[2-(1H- 1,2,4-Trizole-1-yl)ethyl]-1H-Benzimidazole Hemihydrate

ZHANG Zhong, HU Kun, LIN Xin-liang, SUN Ying-ying   

  1. Key Laboratory for the Chemistry and Molecular Engineering ofMedicinal Resources,Ministry of Education of China, College of Chemistry and Chemical Engineering,Guangxi Normal University,Guilin Guangxi 541004,China
  • Received:2012-11-03 Online:2013-03-20 Published:2018-11-26

Abstract: The hemihydrate of an unsymmetrical bisheterocyclic compound 2-[2-(1H-1,2,4-trizole-1-yl)ethyl]-1H-benzimidazole was prepared through the condensation of 1H-1,2,4-triazole-1-propionic acid with o-phenylenediamine,whichwas characterized by elemental analysis,infrared spectra,fluorescence spectra and X-raysingle-crystal diffraction.The compound belongs to orthorhombic system,spacegroup Pbcn with cell parameters:a=2.873 55(13) nm,b=0.766 68(3) nm,c=1.011 59(4) nm,β=90°,V=2.228 62(15) nm3 and Z=4.In the solid state,the bisheterocyclicmolecule adopts an anti conformation with the C7—C8—C9—N3 torsion angle being 174.30(19)°.Two N atoms of the benzimidazole moiety participate in the formation of a set of N—H…N hydrogen bonding interactions,whichjoin the adjacent bisheterocyclic molecules to form a 1-D supramolecular chain.Two such chains are further assembled into a 1-D supramolecular tape via O—H…N hydrogen bonds with the lattice water molecules.

Key words: bisheterocyclic compound, synthesis, crystal structure, spectroscopic study

CLC Number: 

  • O626.2
[1] BUCHENAUER H.Mode of action of triadimefon in Ustilago avenae[J].Pestic Biochem Physiol,1977,7(4):309-320.
[2] SWEEDEN M B,McLEOD P J.Systemic toxicity and field efficacy of imidacloprid,pymetrozine,and triazamate against Myzus persicae (Homoptera:Aphididae) onspinach[J].J Agric Entomol,1997,14(4):421-433.
[3] 徐维明,宋宝安,杨松,等.三唑类化合物除草活性研究进展[J].农药,2010,49(9):625-634.
[4] BALLET S,SALVADORI S,TRAPELLA C,et al.New 2',6'-dimethyl-L-tyrosine (Dmt) opioid peptidomimetics based on the Aba-Gly scaffold.Development of uniqueμ-opioid receptor ligands[J].J Med Chem,2006,49(13):3990-3993.
[5] GÜVEN öö,ERDOGAN T,GöKER H,et al.Synthesis and antimicrobial activityof some novel phenyl and benzimidazole substituted benzyl ethers[J].Bioorg Med Chem Lett,2007,17(8):2233-2236.
[6] BRUNO R D,NJAR V C.Targeting cytochrome P450 enzymes:a new approach inanti-cancer drug development[J].Bioorg Med Chem,2007,15(15):5047-5060.
[7] CHU Wen-juan,WU Ben-lai,TANG Ming-sheng,et al.A novel dodecanuclear cadmium(Ⅱ) macrocycle with a 3D framework:synthesis,structure and properties[J].Cryst Eng Comm,2012,14(13):4414-4419.
[8] CHU Wen-juan,LOU Xin-hua,WANG Zhi-yuan,et al.Self-assemblyof three supramolecular architectures based on an unsymmetrical N-heterocyclic ligand[J].JCoord Chem,2011,64(24):4373-4382.
[9] WILEY R H,SMITH N R,JOHNSON D M,et al.Conjugate addition reactions of azoles.Ⅱ.1,2,4-triazole,tetrazole,nitropyrazole,and benzotriazole[J].J Am Chem Soc,1955,77(9):2572-2573.
[10] SHELDRICK G M.SHELXS-97,program for the solution of crystal structures[CP/CD].Göttingen:University of Göttingen,1997.
[11] SHELDRICK G M.SHELXL-97,program for the refinement of crystalstructures[CP/CD].Göttingen:University of Göttingen,1997.
[12] 郭洪声,周广彦,王瑾玲,等.一水合硝酸三(2-苯并咪唑亚甲)胺合锌(Ⅱ)的合成及晶体结构[J].化学研究与应用,1999,11(2):146-149.
[13] 易平贵,王涛,周继明,等.2-(3-羟基-2-吡啶基)-苯并咪唑的合成、晶体结构及光谱研究[J].化学学报,2009,67(24):2803-2808.
[14] ZHANG Zhong,LU Wei,WU Di-feng.1-[2-(1H-benzimidazol-2-yl)ethyl]-1H-1,2,3-benzotriazole[J].Acta Cryst E,2011,E67(12):O3167.
[15] 杨兵,马於光,沈家骢.π-共轭分子堆积、光电性能与超分子调控[J].高等学校化学学报,2008,29(12):2643-2658.
[1] XIE Tingting, XIE Yao, NI Qingling. Synthesis, Characterization and Crystal Structures of Complexes ContainingOrganic Phosphine Gold Acetylene and Triazoles [J]. Journal of Guangxi Normal University(Natural Science Edition), 2020, 38(4): 92-99.
[2] XU Peng, LI Chaofeng, CHANG Xinwei, ZHANG Yanwu. Synthesis of Water-Soluble Ketone-Aldehyde Resins by Catalysis of Solid Base [J]. Journal of Guangxi Normal University(Natural Science Edition), 2020, 38(3): 70-79.
[3] HUANG Xueren, ZHAO Zhiyuan, JIANG Yimin. Synthesis, Crystal Structure and Luminescent Properties ofa New 2D Coordination Polymer of Zn(Ⅱ)-ttp(4′-(4-carboxyphenyl) -2,2′:6′,2″-terpyridine) [J]. Journal of Guangxi Normal University(Natural Science Edition), 2016, 34(2): 98-104.
[4] WANG Yana, LIN Jiahuang, NI Qingling, ZHANG Fang, YU Ronghua, WANG Xiujian. Synthesis and Crystal Structure of 2-[1,3-bis(2-hydroxy benzyl)-5-pyridyl-4-imidazolidinyl] phenol [J]. Journal of Guangxi Normal University(Natural Science Edition), 2016, 34(2): 105-110.
[5] LIU Han-fu, MA Xian-li, CHEN Su-yi , SHEN Xue-song, HUANG Fu-ping. Synthesis and Antibacterial Activity of Ternary Zinc Complex [J]. Journal of Guangxi Normal University(Natural Science Edition), 2015, 33(4): 103-107.
[6] LIANG Xiao-long, HUANG Wan-yun, PAN Cheng-xue, SU Gui-fa. Synthesis and Crystal Structure of Ethyl 5-acetamido-4-(4-chlorophenyl)-2-methyl-6-oxo-5, 6-dihydro-4H-pyran-3-carboxylate [J]. Journal of Guangxi Normal University(Natural Science Edition), 2015, 33(2): 82-87.
[7] JIANG Li-ping, HUANG Wan-yun, LIU Dong-cheng, LIANG Fu-pei. Synthesis and Crystal Structures of Zn(Ⅱ) and Cu(Ⅱ) Complexes of 2,2′-dihydroxy[1,1′-binaphthalene]-3,3′-dicarbonylbis(salicylaldehydehydrazone) [J]. Journal of Guangxi Normal University(Natural Science Edition), 2015, 33(1): 93-98.
[8] HUO Hong-yue, LI Zhong-qing, QIN Qi-pin, LIU Yan-cheng, CHEN Zhen-feng. Crystal Structure and Antitumor Activity of Zinc(Ⅱ) Complex with Schiff Bases Derived from 2-Hydroxy-3-methoxybenzaldehyde and 2-(3,4-Methylenedioxyphenyl) ethylamine [J]. Journal of Guangxi Normal University(Natural Science Edition), 2014, 32(3): 65-73.
[9] ZHENG Qing-si, LIN Mei-fang, TANG Huang. Synthesis of N-Methyl Moxifloxacin Hydrochloride and Its Application in Production [J]. Journal of Guangxi Normal University(Natural Science Edition), 2014, 32(2): 101-105.
[10] WU Rui, ZHANG Nan-xi, ZHANG Xiao. Synthesis,Structural Characterization and Magnetic Property of Cu[N(CH2OH)2CH2O](SCN) [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(4): 78-83.
[11] HUA Shi-xian, WANG Ying-chun, LI Ya-jun, WANG Heng-shan. Synthesis and Optical Properties of 12-Aryl Substituted Derivatives of Methyl Dehydroabietate [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(2): 64-68.
[12] ZENG Jian-qiang, LIANG Guang-ming, HUANG Ying-da, YANG Kun-guo, GUI Liu-cheng, NI Qing-ling. Hydrogen-bonding Directed Three-dimensional Supramolecular Structure in Catena-((μ2-4,4'-bipyridine)-tetraaqua-cobalt(Ⅱ) bis (2-methylbenzimidazolium-1,3-diacetate) dehydrate): Synthesis and Crystal Structural Characterization [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(2): 69-75.
[13] SHENG Liang-bing, SHEN Yan-ling, XIONG Bo-pi, ZOU Hua-hong, LIANG Fu-pei. Synthesis,Crystal Structure and Magnetic Properties of [Mn3(oba)3(DMF)4] [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(2): 76-80.
[14] CHEN Si-yuan, YANG Yang, PENG Yan, LIU Yan-cheng. Crystal Structure and Antitumor Activity of a New Schiff Base Palladium Complex [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(2): 81-86.
[15] LI Hai-ye, JIANG Yi-min, MENG Xiu-jin. Synthesis and Crystal Structure of Phenanthroline-Cysteic Acid Cobalt(Ⅱ) Ternary Complex [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(1): 72-75.
Viewed
Full text


Abstract

Cited
  Shared   
  Discussed   
No Suggested Reading articles found!
Copyright © Journal of Guangxi Normal University(Natural Science Edition), All Rights Reserved.
Tel: 0773-5857325　E-mail: gxsdzkb@mailbox.gxnu.edu.cn
Powered by Beijing Magtech Co. Ltd