Synthesis, characterization and crystal structure of 1-ferrocenesulfonyl-2-long carbon chain alkyl benzimidazole

doi:10.1007/s11458-009-0008-9

Front Chem Chin

2009, Vol. 4

Issue (1) : 52-57 https://doi.org/10.1007/s11458-009-0008-9

RESEARCH ARTICLE

Synthesis, characterization and crystal structure of 1-ferrocenesulfonyl-2-long carbon chain alkyl benzimidazole

Junzhen ZHANG, Bingqin YANG(

), Yating YANG, Binglin ZHANG

Department of Chemistry, Northwest University, Xi’ an 710069, China

Download: PDF(175 KB) HTML
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract

Six new 1-ferrocenesulfonyl-2-benzimidazole derivatives were prepared by the reaction of ferrocenesulfonyl chloride with benzimidazole derivatives in the presence of dichloromethane and n-tetrabutylammonia bromide. The yields of these six new ferrocenesulfonyl benzimidazole derivatives were about 80%. The structures characteristic were confirmed by IR, ¹H-NMR, Elemental analysis and MS. The crystal structure of compound a₂ was determined via X-ray single crystal diffraction and it belongs to monoclinic system with space group C2/c, and the unit cell parameters are α = 2.8252(2) nm, b = 0.97696(7) nm, c = 1.64828(12) nm, α = 90°, β = 92.053(2)°, γ = 90°, V = 4.5466(6) nm³, Z = 8, F (000) = 2024, Mr =481.40, Dc = 1.407 g/cm³, μ = 0.784 mm^–1, R₁ = 0.0495, wR₂ = 0.1517. The results show that the reactions of 2-alkylbenzimidazoles containing active hydrogen with ferrocenesulfonyl chloride gave 1-ferrocenesulfonyl-2-alkylbenzimidazoles in good yields.

Keywords ferrocenesulfonyl benzimidazol synthesis characteristic crystal structure

Corresponding Author(s): YANG Bingqin,Email:yangbq@nwu.edu.cn

Issue Date: 05 March 2009

Cite this article:

Yating YANG,Binglin ZHANG,Junzhen ZHANG, et al. Synthesis, characterization and crystal structure of 1-ferrocenesulfonyl-2-long carbon chain alkyl benzimidazole[J]. Front Chem Chin, 2009, 4(1): 52-57.

URL:

https://academic.hep.com.cn/fcc/EN/10.1007/s11458-009-0008-9
https://academic.hep.com.cn/fcc/EN/Y2009/V4/I1/52

Fig.1 The synthetic route of 1-ferrocenesulfonyl-2-alkylbenzimidazole

Tab.1 Crystal data and structure refinement for the compound

Fig.2 Crystal structure of compound

Fig.3 Molecular packing of the title compound

Tab.2 Selected bond lengths (nm) and angles (°) for the compound

1	Sirtori V, Lombardi L, Redaelli G. Chemical composition and thermal stability of 2 butyl, 5 chloro, benzimidazole film. J Electronic Mater , 1997, 5: 459 doi: 10.1007/s11664-997-0119-3
2	Wu Y T, Liu M H. Langmuir films of 2-alkyl benzimidazoles on aqueous AgNO₃ Subphase and the layer structures of the transferred films. Chinese J Inorg Chem , 2004, 20(5): 449
3	Takao O, ShinichiA.Water-soluble prefluxes, printed circuit boards, and surface-treatment of metal surface. JP 09 176 871, 1997
4	George M W, Donald A M, Parker J L. IPC PR INTED CIRCU ITS EXPO, 1994
5	Shi Z X, Pang Z Z. An investigation of the thermal stability of 2-Alkylbenzoimidazole on copper. Chem J Chinese Univ , 2000, 21(4): 586
6	Yoshida S, Ishida H. An investigation of the thermal stability of undecylimidazole on copper by FT-IR reflection-absorption spectroscopy. Appl Surface Sci , 1995, 89: 39 doi: 10.1016/0169-4332(95)00006-2
7	Hideeki Y. Process for production of copper through-hole printed wiring boards. US 5275694, 1994
8	Lu Y H, Pang Z Z, Wang L, Shi Z X. An investigation of the thermal stability of 2-Alkylbenzoimidazole on copper. Therm Osetting Resin , 2003, 18(6): 1
9	Pan Y Y. Modification of imidazole and application of modified imidazole to epoxy resin. Therm Osetting Resin , 2001, 16(4): 21
10	Ao J P, Sun G Z, Zeng W M. Progress of research for corrosion inhibitors of cleaning in hydrochloric acid. J Nanchang Inst Aeronautical Tech , 2000, 14 (1): 50
11	Zhou X X, Liu J P. Present state of the application of corrosion inhibitors to acid pickling and its development trend. Ind Water Treatment , 2002, 22 (1): 16
12	Zheng J S, Huang K Y. Review and prospect of corrosion inhilitor development. Mater Prot , 2000, 33 (5) : 11
13	Stupnisek-Lisac E, Bozic Loncaric A, Cafuk I. Low-toxicity copper corrosion inhibitors. Corrosion , 1998, 9: 713
14	Lahou M, Weliou M, Salem M, Hajji M S. Synthesis and insecticidal activity of some benzimidazolic and benzothiazolic derivatives. Annales Pharm aceutiques Francaises , 2003, 61 (1): 57
15	Edwards E I, Epton R, Marr G. 1,1'-Ferrocenyldiacetic acid anhydride and its use in the preparation of heteroannularly substituted ferrocenyl-penicillins and -cephalosporins. J Oganom et Chem , 1976, 107 (3): 351 doi: 10.1016/S0022-328X(00)91527-4
16	Robert D, Julio S. Unsymmetrically-1,3-disubstituted ferrocene-containing thermotropic liquid crystals: A new family of chiral metallomesogens. Tetrahedron Lett , 1994, 35 (14): 2169 doi: 10.1016/S0040-4039(00)76787-6
17	Dombrowski K E, Baldwin W, Sheats J E. Metallocenes in biochemistry, microbiology & medicine. J Org-m et Chem , 1986, 302: 281 doi: 10.1016/0022-328X(86)80097-3
18	Si N G, Zhang Z J, Liu J L, Li Z N, Zhang D M, Chen L, Wang L Z. Biological activity and application of a novel fungicide. Chinese J Pesticides , 2004, 43 (1): 16
19	Li M, Yang B Q, Zhu A L, Bai Y J, LU Jun, Shi Z. Synthesis of nitrogen heterocycle ferrocenesulfonyl amide. J Northwest Univ (Nat Sci Edi) , 2004, 34 (6): 680
20	Slocum D W, Achermann W. The preparation of several N-substituted and N,N-disubstitute, ferrocenesulfonamides. Synth React Inorg Met-Org Chem , 1982, 12 (4): 397 doi: 10.1080/00945718208063123
21	Pool W O, Harwood H J, Ralston A W. 2-Alkylbenzimidazoles as derivatives for the identification of aliphatic acids. J Am Chem Soc , 1937, 59: 128 doi: 10.1021/ja01280a044
22	Suo R, Wang G, Pang Z Z. Synthesis and characterization of 2 alkyl substituted benzimidazoles. J Beijing Univ Chem Tech , 1999, 26 (1): 27

[1]	Qiuyang SUN, Zhipan LIU. Mechanism and kinetics for methanol synthesis from CO₂/H₂ over Cu and Cu/oxide surfaces: Recent investigations by first-principles-based simulation[J]. Front Chem Chin, 2011, 6(3): 164-172.
[2]	Bo LIU, Duo FAN, Qiong ZHANG, Yu CHEN, Weihong ZHU, . A novel NIR violanthrone derivative with high electron-deficiency: effect of fluorescence on dicyanomethylene substitution[J]. Front. Chem. China, 2010, 5(2): 200-207.
[3]	Xiaojing LU, Yin PENG, . The first rare-earth fluoride one-dimensional nanostructures: template synthesis of LnF 3 (Ln=Eu, La) nanotubes[J]. Front. Chem. China, 2010, 5(1): 76-79.
[4]	Zhenhai LIU, Hongfei LI, . Application to polymer characterization by thermal analysis[J]. Front. Chem. China, 2009, 4(4): 352-359.
[5]	Yanli SUN, Shiming WANG, Qiongsheng WANG. Flowerlike MoS₂ nanoparticles: solvothermal synthesis and characterization[J]. Front Chem Chin, 2009, 4(2): 173-176.
[6]	Fanzuo KONG. Synthesis of plant arabinogalactans[J]. Front Chem Chin, 2009, 4(1): 10-31.
[7]	Bozhou WANG, Weipeng LAI, Qian LIU, Peng LIAN, Yongqiang XUE. Synthesis, characterization and quantum chemistry study of 3,6-bis(1H-1,2,3,4-tetrazol-5-yl-amino)-1,2,4,5-tetrazine[J]. Front Chem Chin, 2009, 4(1): 69-74.
[8]	PENG Yin, BAO Ling. Controlled-synthesis of ZnO nanorings[J]. Front. Chem. China, 2008, 3(4): 458-463.
[9]	WANG Cunwen, CHEN Wen, WANG Weiguo, WU Yuanxin, ZHANG Junfeng, YU Chuanbo. Calculation of partial molar volume of components in supercritical ammonia synthesis system [J]. Front. Chem. China, 2008, 3(4): 489-494.
[10]	LIU Xinhua, ZHU Jing, PAN Chunxiu, LI Bo, SONG Bao‘an. Synthesis and fungicidal activity of novel 3,5-diarylpyrazole derivatives[J]. Front. Chem. China, 2008, 3(4): 418-421.
[11]	LIU Pengyan, LIU Lei, ZHANG Li, JIANG Ning, LIU Zhanli, WANG Yun. Synthesis and characterization of molecularly imprinted polymers for recognition of ciprofloxacin[J]. Front. Chem. China, 2008, 3(4): 378-383.
[12]	HE Xiaoli, LU Lude, WANG Xin, YANG Xujie, HE Xiaoli, GUO Xuan. Synthesis and catalytic properties of tetraorganodistannoxanes containing silicon[J]. Front. Chem. China, 2008, 3(4): 413-417.
[13]	HE Gu, GUO Li, WANG Qianqian, MA Lifang, HE Zechao. Studies on synthesis and molecular dynamics simulation of dendrimers containing amino acids and peptides[J]. Front. Chem. China, 2007, 2(4): 378-382.
[14]	WU Yikang, WU Yu-Lin. A new era for organic synthesis—highlights of the recent progress[J]. Front. Chem. China, 2007, 2(3): 227-264.
[15]	YANG Yuan, LI Qi, ZHANG Jinnan, SONG Xiaohong, LUO Surong. Synthesis and crystal structure of inclusion compounds: Trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid with boric acid and tetrabutylammonium salt[J]. Front. Chem. China, 2007, 2(3): 296-302.

Viewed

Full text

Abstract

Cited

Shared

Discussed