Chinese Journal of Magnetic Resonance ›› 2004, Vol. 21 ›› Issue (4): 419-425.

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STRUCTURE ELUCIDATION OF NAPHTHOLIC NAPHTHALENE SULFONATE BY NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY

 ZHANG Wei, JIN Kun, PENG Qi-Ji, ZHAO De-Feng*   

  1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116012, China
  • Received:2004-03-19 Revised:2004-05-25 Online:2004-12-05 Published:2004-12-05
  • Supported by:

    国家自然科学基金资助项目(20172012).

Abstract:

Naphtholic naphthalene sulfonate containing tertiary amine group and its derivatives can be used to synthesize universal dyes, cationic dyes and acid dyes. According to the literatures, it can be obtained by condensation of 7-acetamide-4-hydroxy-2-naphthalenesulfonyl chloride with N, N-dimethylethylenediamine, followed by esterfication of the hydroxyl group using excessive sulfonyl chloride in -N, N-dimethylformamide (DMF) in the presence of pyridine. In this paper, an inexpensive synthesis method for naphtholic naphthalene sulfonate is described, the required operations in which are also more convenient as compared with the former methods. Naphtholic naphthalene sulfonate were prepared by treating-N, N-dimethylethylenediamine with 7-acetamide-4-hydroxy-2-naphthalenesulfonyl chloride in acetonitrile in the presence of K2CO3. The structure of the compound was elucidated by 1D 1H and 13C NMR and two-dimensional NMR spectroscopy including gCOSY, TOCSY, gHMBC and gHSQC. The complete 1H and 13Cchemical shifts and the 1H-1H coupling constants were obtained.

Key words: Naphtholic naphthalene sulfonate, Two-dimensional NMR spectroscopy, chemical shift assignment

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