tetraethylammonium picrate | 741-03-7

• 英文名称: tetraethylammonium picrate
• 英文别名: tetraethylammonium 2,4,6-trinitrophenolate；tetra-n-ethyl-ammonium picrate；tetra-n-ethylammonium picrate；Picrinsaeure; Tetraaethylammonium-picrat；Tetraethylammonium pikrat；Tetraethylammonium-pikrat；tetraethylazanium;2,4,6-trinitrophenolate
• CAS: 741-03-7
• 化学式: C₆H₂N₃O₇*C₈H₂₀N
• 分子量: 358.351
• InChiKey: OHHISBPTUZYIHD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  四乙基溴化铵 、 苦味酸 在 2-氯吡啶 作用下， 以 乙腈 为溶剂， 以87%的产率得到tetraethylammonium picrate
  参考文献：
  名称：

  盐对乙腈中硝基苯酚向胺或吡啶碱的质子转移的影响

  摘要：

  The addition of MQO(4) (M(+) = Li+ and Na+) to 1.0 x 10(-4) mol dm(-3) 2,4-dinitrophenol and the equivalent concentration of gamma-picoline (4-methylpyridine) in acetonitrile caused a promoted proton transfer from the phenol to the base to the extent of 62 and 23% for 0.1 mol dm(-3) Li+ and Na+, respectively. Alkaline-earth metal perchlorates (M(ClO4)(2)) had larger effects even at low concentrations of M(2+), e.g., the proton-transfer ratio was 90% for 1.0 x 10(-2) mol dm(-3) Mg(ClO4)(2). The effects of M(2+) decreased with increasing size of the cation: Mg2+ > Ca2+ > Sr2+, Ba2+. With the addition of MClO(4) or M(ClO4)2, a higher proton transfer ratio was observed for 2,5-dinitrophenol + gamma-collidine than for 2,4-dinitrophenol + gamma-picoline. The salt effects of MClO(4) or M(ClO4)(2) on the acid-base reactions were accounted for by the formation of triple cations or complex species of M(+) or M(2+) With the phenolate ions (B represents base): (NO2)(2)PhOH-B + 2M(+) reversible arrow (NO2)(2)PhO(-)(M(+))(2) + BH+; (NO2)(2)PhOH-B + M(2+) reversible arrow (NO2)(2)PhO(-)M(2+) + BH+. The stronger the base, the greater the proton transfer (based on the addition of salts) from the phenols. The effects of LiClO4 on 2,4,6-trinitrophenol (picric acid) + 2-chloropyridine were very small; however, the effects on the proton transfer from 2- and 4-nitrophenol to triethylamine were very large. The extent of the proton transfer (based on the addition of LiClO4) from nitrophenols in the presence of appropriate bases was coincident with the order of the formation constants of ion aggregates (ion pairs and triple ions) for lithium nitrophenolates in acetonitrile: 2- '' 4-, 2,5- > 2,4- '' 2,4,6-. The ''free'' phenolate ions were produced by the addition of tetraalkylammonium halides (R(4)N(+)X(-): R = Et, n-Bu; X(-) = Cl-, Br-, I-) to the nitrophenols in the presence of bases in acetonitrile: (NO2)(n)PhOH-B + 2X(-) reversible arrow (NO2)(n)PhO(-) + BH+(X)(2). The presence of a base was not essential for the deprotonation of picric acid with R(4)NX.

  DOI：

  10.1021/j100045a020

文献信息

• DE545430
  申请人：——

  公开号：——

  公开（公告）日：——
• Quantitative treatment of bromide ion nucleophilicity in a microemulsion
  作者：Clifford A. Bunton、Francesco De Buzzaccarini

  DOI：10.1021/j100222a033

  日期：1982.12
• Ionic equilibriums in pyridine-iodine solutions
  作者：S. Aronson、P. Epstein、D. B. Aronson、G. Wieder

  DOI：10.1021/j100395a041

  日期：1982.3