Synthesis, spectral and structural study of N-[1-(N,N,N′,N′-tetramethylphosphoramidoyl)1H-benzimidazol-2-yl]-propionimidic ethyl ether

被引:1
|
作者
Raouafi, N
Freytag, M
Jones, PG
Boujlel, K
BenKhoud, ML
机构
[1] Univ Tunis El Manar, Fac Sci, Lab Chim Analyt & Electrochim, El Manar 2092, Tunisia
[2] Tech Univ Braunschweig, Inst Anorgan & Analyt Chem, D-38023 Braunschweig, Germany
关键词
N-(N-1-phosphoramido-benzimidazolyl)-N '-imidate; phosphoroamidation; X-ray structure determination; conformation; weak" hydrogen bonds;
D O I
10.1007/s11224-005-2848-3
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The preparation of N-[1-(N, N, N', N'-tetramethylphosphoramidoyl)-1H-benzimidazol-2-yl]-proponimidic ethyl ester 2 has been achieved by the reaction of N-(1H-benzimidazol-2-yl)-proponimidic acid ethyl ester 1 with N, N, N', N'-tetramethylchlorophosphoramide. The structure of compound 2 has been determined by X-ray diffraction. The results of (H-1, C-13, P-31) NMR, IR, EI-MS spectral data are consistent with those obtained from the X-ray diffraction. The compound crystallizes in the triclinic system, following the EsZ conformation. In the crystal, there are two weak C3-H3 center dot center dot center dot 1 and C15-H15 center dot center dot center dot O1 intermolecular hydrogen bonds.
引用
收藏
页码:169 / 172
页数:4
相关论文
共 50 条
  • [1] Synthesis, Spectral and Structural Study of N-[1-(N,N,N′,N′-Tetramethylphosphoramidoyl)- 1H-Benzimidazol-2-yl]-Propionimidic Ethyl Ether
    N. Raouafi
    M. Freytag
    P. G. Jones
    K. Boujlel
    M. L. BenKhoud
    Structural Chemistry, 2005, 16 : 169 - 172
  • [2] Synthesis, spectroscopic and structural studies of N-(1H-benzimidazol-2-yl)-N′-benzyl propionamidine
    Raouafi, N.
    Freytag, M.
    Jones, P. G.
    BenKhoud, M. L.
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2007, 37 (06) : 381 - 386
  • [3] Synthesis, spectroscopic and structural studies of N-(1H-benzimidazol-2-yl)-N′-benzyl propionamidine
    N. Raouafi
    M. Freytag
    P. G. Jones
    M. L. BenKhoud
    Journal of Chemical Crystallography, 2007, 37 : 381 - 386
  • [4] Metal chelates of N-benzothiazol-2-yl-, N-benzoxazol-2-yl- and N-(1H-benzimidazol-2-yl)-benzamide
    Angulo-Cornejo, J
    Lino-Pacheco, M
    Richter, R
    Hennig, L
    Hallmeier, KH
    Beyer, L
    INORGANICA CHIMICA ACTA, 2000, 305 (01) : 38 - 45
  • [5] Synthesis and reactvity of N-[N-phosphoramido-1H-benzimidazol-2-YL] imidates
    Raouafi, N
    Boujlel, K
    Benkhoud, ML
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (12) : 2471 - 2482
  • [6] {N-[1-(1H-Benzimidazol-2-yl)ethylidene-κN3]-3-(1H-imidazol-1-yl)propan-1-amine-κN}dibromidomercury(II)
    Wang, Qing
    Fu, Zhong-Ye
    Yu, Liang-Min
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68 : M44 - +
  • [7] catena-Poly[[(diiodidocadmium)-μ{1-[(1H-benzimidazol-2-yl)methyl]-1H-imidazole-κ2N:N′}] N,N-dimethyl-formamide monosolvate]
    Liu, Bingtao
    Zhao, Lei
    Li, Ting
    Meng, Xiangru
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : M1901 - U1283
  • [8] N,N,N′,N′-Tetrakis[(1H-benzimidazol-2-yl)methyl]-ethane-1,2-diamine glycol disolvate
    Qin, SD
    Feng, SS
    Zhang, HM
    Yang, P
    Zhu, ML
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 : O1121 - O1122
  • [9] 2-(1H-Benzimidazol-2-yl)-N-[(E)-(dimethylamino)methylidene]benzene-sulfonamide
    Ashraf, Adnan
    Tahir, M. Nawaz
    Siddiqui, Waseeq Ahmad
    Perveen, Nadia
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O2069 - +
  • [10] Synthesis, Characterization, and Molecular Docking Study of N-[4-(1H-Benzimidazol-2-yl)-1,3-thiazol-2-yl]-1-[(E)-phenyldiazenyl)-1-phenylmethanimines
    S. Ramakrishna Reddy
    G. Ganga Reddy
    Ch. Venkata Ramana Reddy
    E. Laxminarayana
    Russian Journal of Organic Chemistry, 2022, 58 : 858 - 864