Nicotinoylglykolsaeure-ethylester | 1208-24-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Nicotinoylglykolsaeure-ethylester
• 英文别名: 3-Pyridinecarboxylic acid,2-ethoxy-2-oxoethyl ester；(2-ethoxy-2-oxoethyl) pyridine-3-carboxylate
• CAS: 1208-24-8
• 化学式: C₁₀H₁₁NO₄
• mdl: MFCD10474169
• 分子量: 209.202
• InChiKey: YUUIEDSBFGGALC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  烟酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 Nicotinoylglykolsaeure-ethylester
  参考文献：
  名称：

  Relationship between Chemical Structure and Supramolecular Effective Molarity for Formation of Intramolecular H-Bonds

  摘要：

  Effective molarity (EM) is a key parameter that determines the efficiency of a range of supramolecular phenomena from the folding of macromolecules to multivalent ligand binding. Coordination complexes formed between zinc porphyrins equipped H-bond donor sites and pyridine ligands equipped with H-bond acceptor sites have allowed systematic quantification of EM values for the formation of intramolecular H-bonds in 240 different systems. The results provide insights into the relationship of EM to supramolecular architecture, H-bond strength, and solvent. Previous studies on ligands equipped with phosphonate diester and ether H-bond acceptors were inconclusive, but the experiments described here on ligands equipped with phosphine oxide, amide, and ester H-bond acceptors resolve these ambiguities. Chemical double-mutant cycles were used to dissect the thermodynamic contributions of individual H-bond interactions to the overall stabilities of the complexes and hence determine the values of EM, which fall in the range 1-1000 mM. Solvent has little effect on EM, and the values measured in toluene and 1,1,2,2-tetrachloroethane are similar. For H-bond acceptors that have similar geometries but different H-bond strengths (amide and ester), the values of EM are very similar. For H-bond acceptors that have different geometries but similar H-bond strengths (amide and phosphonate diester), there is, little correlation between the values of EM. These results imply that supramolecular EMs are independent of solvent and intrinsic H-bond strength but depend on supramolecular architecture and geometric complementarity.

  DOI：

  10.1021/ja406235d

文献信息

• Quantification of the Effect of Conformational Restriction on Supramolecular Effective Molarities
  作者：Harry Adams、Elena Chekmeneva、Christopher A. Hunter、Maria Cristina Misuraca、Cristina Navarro、Simon M. Turega

  DOI：10.1021/ja310221t

  日期：2013.2.6

  H-bonding interactions to the overall stability of the complexes. Measurement of association constants for the corresponding intermolecular H-bonding interactions allowed determination of the effective molarities (EM) for the intramolecular interactions. Comparison of ligands that feature amide H-bond acceptors and ester H-bonds at identical sites on the ligand framework show that the values of EM are

  已在两种不同的溶剂、甲苯和 1,1,2,2-四氯乙烷 (TCE) 中测量了 96 个密切相关的锌卟啉-吡啶配体配合物的缔合常数。锌卟啉受体具有苯酚侧臂，可与吡啶配体上的酯或酰胺侧臂形成分子内H键。这些结合常数用于构建 64 个化学双突变循环，测量分子内 H 键相互作用对复合物整体稳定性的自由能贡献。测量相应分子间氢键相互作用的缔合常数可以确定分子内相互作用的有效摩尔浓度 (EM)。在配体框架上的相同位点具有酰胺 H 键受体和酯 H 键的配体的比较表明，EM 的值实际上是相同的。类似地，EM 值在甲苯和 TCE 中几乎相同。然而，比较两个扭转自由度不同的配体系列表明，柔性配体的 EM 值比相应的刚性配体低一个数量级。该观察结果适用于具有不同程度受体-配体互补性的一系列不同超分子结构，并表明通常在超分子复合物中冷冻转子的成本约为 5 kJ/mol。然而，比较两个扭转自由度不同的配体系列表明，柔性配体的
• Relationship between Chemical Structure and Supramolecular Effective Molarity for Formation of Intramolecular H-Bonds
  作者：Hongmei Sun、Christopher A. Hunter、Cristina Navarro、Simon Turega

  DOI：10.1021/ja406235d

  日期：2013.9.4

  Effective molarity (EM) is a key parameter that determines the efficiency of a range of supramolecular phenomena from the folding of macromolecules to multivalent ligand binding. Coordination complexes formed between zinc porphyrins equipped H-bond donor sites and pyridine ligands equipped with H-bond acceptor sites have allowed systematic quantification of EM values for the formation of intramolecular H-bonds in 240 different systems. The results provide insights into the relationship of EM to supramolecular architecture, H-bond strength, and solvent. Previous studies on ligands equipped with phosphonate diester and ether H-bond acceptors were inconclusive, but the experiments described here on ligands equipped with phosphine oxide, amide, and ester H-bond acceptors resolve these ambiguities. Chemical double-mutant cycles were used to dissect the thermodynamic contributions of individual H-bond interactions to the overall stabilities of the complexes and hence determine the values of EM, which fall in the range 1-1000 mM. Solvent has little effect on EM, and the values measured in toluene and 1,1,2,2-tetrachloroethane are similar. For H-bond acceptors that have similar geometries but different H-bond strengths (amide and ester), the values of EM are very similar. For H-bond acceptors that have different geometries but similar H-bond strengths (amide and phosphonate diester), there is, little correlation between the values of EM. These results imply that supramolecular EMs are independent of solvent and intrinsic H-bond strength but depend on supramolecular architecture and geometric complementarity.