Tetrabutylammonium 4-methylphenolate | 82101-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Tetrabutylammonium 4-methylphenolate
• 英文别名: 4-Methylphenolate;tetrabutylazanium
• CAS: 82101-85-7
• 化学式: C₇H₇O*C₁₆H₃₆N
• 分子量: 349.601
• InChiKey: RMCDNCKVVHTEQK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.07
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  23.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-(4-氰基苯基)偶氮苯基硫化物 、 Tetrabutylammonium 4-methylphenolate 以69%的产率得到
  参考文献：
  名称：

  PETRILLO, GIOVANNI;NOVI, MARINO;CARLO, DELLERBA, TETRAHEDRON LETT., 30,(1989) N9, C. 6911-6912

  摘要：

  DOI：

文献信息

• Active site of bacteriorhodopsin. FTIR and 1H NMR studies using a model molecule
  作者：Bogumil Brzezinski、Jerzy Olejnik、Georg Zundel

  DOI：10.1039/ft9949001095

  日期：——

  We obtained the 2-N-methylaminoethylguanidine amide, 4, of Kemp's triacid(all-cis-1,3,5-trimethylcyclohexane 1,3,5-tricarboxylic acid) as a model substance for the active site of bacteriorhodopsin. Compound 4 was synthesised from Kemp's triacid triethyl ester, 1, in three reactions. Compound 4 and its complex with tetrabutylammonium 4-methylphenolate were studied by FTIR and 1H NMR spectroscopy in acetonitrile solutions. In the case of compound 4, two types of hydrogen bond are formed: one is the CO2H⋯N⇌CO–2⋯H+N bond. In this case, the donor is one of the two carboxylic acid groups, and the acceptor, the guanidine group. A double-minimum proton potential is present in this bond and therefore it exhibits large proton polarizability. The second NH⋯OC hydrogen bond formed between the protonated guanidine (proton donor group) and the carbonyl O atom of the other carboxylic group is asymmetrical. The proton is localised at the guanidine residue. If a phenolate molecule is added to the solution of compound 4, the situation changes dramatically. A PhOH⋯N⇌PhO–⋯H+N bond with large proton polarizability is formed between the phenolate and guanidine groups. The polarizable carboxylic acid–guanidine hydrogen bond is broken and the asymmetrical NH⋯O bond between guanidine and the O atoms of carboxylic acid becomes much stronger. The results obtained with the model are compared with those obtained earlier with bacteriorhodopsin.

  我们获得了坎普三酸（全顺式-1,3,5-三甲基环己烷-1,3,5-三羧酸）的 2-N-甲基氨基乙基胍酰胺 4，作为细菌眼色素活性位点的模型物质。化合物 4 是由坎普三酸三乙酯 1 通过三个反应合成的。化合物 4 及其与 4-甲基酚酸四丁基铵的复合物在乙腈溶液中通过傅里叶变换红外光谱和 1H NMR 光谱进行了研究。化合物 4 形成了两种类型的氢键：一种是 CO2H⋯N⇌CO-2⋯H+N 键。在这种情况下，供体是两个羧酸基团之一，受体是胍基。该键存在双最小质子势，因此质子极化性较大。质子化的胍基（质子供体基团）和另一个羧基的羰基 O 原子间形成的第二个 NH⋯OC 氢键是不对称的。质子位于胍残基上。如果在化合物 4 的溶液中加入一个苯酚分子，情况就会发生巨大变化。在苯酚基团和胍基团之间形成了一个具有较大质子极化性的 PhOH⋯N⇌PhO-⋯H+N 键。可极化的羧酸-胍氢键被打破，胍和羧酸 O 原子间的不对称 NH⋯O 键变得更强。利用该模型获得的结果与早先利用细菌眼底蛋白获得的结果进行了比较。
• Acid/Base Controllable Molecular Recognition
  作者：Kent A. Nielsen、Steffen Bähring、Jan O. Jeppesen

  DOI：10.1002/chem.201101266

  日期：2011.9.19

  of the host–guest complexation taking place between the TTF‐calix[4]pyrrole receptor and the TNB guests was studied by means of absorption and 1H NMR spectroscopy; this revealed that the conformation of the molecular receptor can be switched between locked and unlocked states by using base and acid as the input. In the unlocked state, the receptor is able to accommodate two TNB guest molecules, whereas

  对超分子受体中可控分子识别的研究对于阐明可导致分子识别应用外部控制的设计策略非常重要。在这项工作中，我们介绍了不对称（TTF）四硫富瓦烯-杯[4]吡咯受体的设计和合成，并表明其对1,3,5-三硝基苯（TNB）的识别可以通过酸/碱输入来控制。新的受体由三个相同的TTF单元和一个附加有苯酚部分的第四TTF单元组成。通过吸收和1研究了TTF-杯[4]吡咯受体和TNB客体之间主客体络合的过程。1 H NMR光谱法；这表明通过使用碱和酸作为输入，可以在锁定状态和解锁状态之间切换分子受体的构象。在解锁状态下，受体能够容纳两个TNB客体分子，而客体在锁定状态下无法与受体结合。这项工作旨在说明受体的外部控制（酸/碱）如何用于指导来宾（TNB）的分子识别。它导致了一个新的可控分子识别系统，该系统可作为酸/碱开关。
• Unsymmetrical biaryls from aryloxide anions and arylazo phenyl sulfides in DMSO
  作者：Giovanni Petrillo、Marino Novi、Carlo Dell'Erba

  DOI：10.1016/s0040-4039(01)93386-6

  日期：1989.1
• PETRILLO, GIOVANNI;NOVI, MARINO;CARLO, DELLERBA, TETRAHEDRON LETT., 30,(1989) N9, C. 6911-6912
  作者：PETRILLO, GIOVANNI、NOVI, MARINO、CARLO, DELLERBA

  DOI：——

  日期：——
• OPTICAL CARBON DIOXIDE SENSORS
  申请人：Novartis AG

  公开号：EP1005645A1

  公开（公告）日：2000-06-07