acetic-d acid | 35223-87-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: acetic-d acid
• 英文别名: acetic acid；2-deuterio-acetic acid；2-Deuterio-essigsaeure；deuteroacetic acid；2-deuterioacetic acid
• CAS: 35223-87-1
• 化学式: C₂H₄O₂
• 分子量: 61.0446
• InChiKey: QTBSBXVTEAMEQO-MICDWDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  acetic-d acid 在 sodium hydroxide 、 对甲苯磺酰氯 作用下， 生成 2-deuterio-acetic acid anhydride
  参考文献：
  名称：

  Reorientational tunneling of partially deuterated methyl groups: A single-crystal deuteron NMR study of aspirin-CH2D

  摘要：

  Partially deuterated methyl groups in single crystals of aspirin are investigated by deuteron NMR at temperatures between 8 K and room temperature. The CH2D groups perform reorientations which are governed by a rotational potential with three wells, two of which are almost equally deep whereas the third is significantly deeper. At temperatures below 20 K, a so far unobserved type of incoherent tunneling process is identified. This process consists in reorientations between the two upper potential wells which are fast on the time scale of the quadrupolar interaction, whereas transitions into the deeper well are slow on this time scale. At temperatures above 35 K, the methyl groups perform thermally activated stochastic reorientations between all three potential wells. By determining the relative populations of the three wells as a function of temperature, the energy difference between the lower and the two upper wells is found to be 3.3 meV. This amounts to almost 8% of the average barrier height, which is determined from the temperature dependence of the spin-lattice relaxation time to be 43 meV.

  DOI：

  10.1063/1.475995
• 作为产物：
  描述：

  2-deuterio-acetic acid methyl ester 在 Dowex-50 cation exchange resin 、 水 作用下， 反应 5.0h， 生成 acetic-d acid
  参考文献：
  名称：

  Reorientational tunneling of partially deuterated methyl groups: A single-crystal deuteron NMR study of aspirin-CH2D

  摘要：

  Partially deuterated methyl groups in single crystals of aspirin are investigated by deuteron NMR at temperatures between 8 K and room temperature. The CH2D groups perform reorientations which are governed by a rotational potential with three wells, two of which are almost equally deep whereas the third is significantly deeper. At temperatures below 20 K, a so far unobserved type of incoherent tunneling process is identified. This process consists in reorientations between the two upper potential wells which are fast on the time scale of the quadrupolar interaction, whereas transitions into the deeper well are slow on this time scale. At temperatures above 35 K, the methyl groups perform thermally activated stochastic reorientations between all three potential wells. By determining the relative populations of the three wells as a function of temperature, the energy difference between the lower and the two upper wells is found to be 3.3 meV. This amounts to almost 8% of the average barrier height, which is determined from the temperature dependence of the spin-lattice relaxation time to be 43 meV.

  DOI：

  10.1063/1.475995
• 作为试剂：
  描述：

  氯仿 在 acetic-d acid 、 锌 作用下， 生成 dichloromethane-d1
  参考文献：
  名称：

  High-field NMR determination of magnetic susceptibility tensors and angular correlation factors of halomethanes

  摘要：

  DOI：

  10.1021/ja00248a009

文献信息

• No Contribution of an Inductive Effect to Secondary Deuterium Isotope Effects on Acidity
  作者：Charles L. Perrin、Agnes Flach

  DOI：10.1002/anie.201102125

  日期：2011.8.8

  Effect and cause: Secondary deuterium isotope effects on the acidity of the deuterated compounds 1–4 were measured by using an NMR titration method applicable to a mixture and capable of very high accuracy. Variable‐temperature experiments show that these isotope effects are due only to changes in vibrational frequencies. These findings refute an inductive origin for these isotope effects.

  效应而引起的在氘化化合物的酸度二次氘同位素效应：1 - 4通过使用适用于混合物中，并能够在非常高的精度的NMR滴定法进行测定。可变温度实验表明，这些同位素效应仅是由于振动频率的变化引起的。这些发现驳斥了这些同位素效应的归因。
• Secondary Deuterium Isotope Effects on the Acidity of Carboxylic Acids and Phenols
  作者：Charles L. Perrin、Yanmei Dong

  DOI：10.1021/ja069103t

  日期：2007.4.1

  Secondary deuterium isotope effects (IEs) on acidities have been accurately measured by an NMR titration method applicable to a mixture of isotopologues. Deuteration definitely decreases the acidity of carboxylic acids and phenols, by up to 0.031 in the DeltapK per D. For aliphatic acids, the IEs decrease as the site of deuteration becomes more distant from the OH, as expected, but a surprising result

  二次氘同位素效应 (IE) 对酸度的影响已通过适用于同位素体混合物的 NMR 滴定方法准确测量。氘化肯定会降低羧酸和酚类的酸度，每 D 的 DeltapK 最多降低 0.031。对于脂肪酸，正如预期的那样，随着氘化位点与 OH 的距离越来越远，IEs 降低，但令人惊讶的结果是 IEs随着氘化位点从邻位移动到间位到对位，苯酚和苯甲酸中的 实验数据得到了从头计算的支持，然而，这大大高估了 IE。差异似乎不是由于溶剂化。IE 起源于同位素敏感振动，其频率和零点能量在去质子化时降低。在最简单的情况下，甲酸盐，关键振动可以被识别为 CH 拉伸，它被氧孤对的离域削弱。对于芳香酸，离域不能解释来自邻、间和对氘的 IE 的近乎恒定性，但观察到的 IE 与计算的振动频率和电子密度一致。此外，频率分析解释 IE 的能力是反对归纳起源的证据。
• Microwave Spectrum of Acetyl Cyanide
  作者：Lawrence C. Krisher、E. Bright Wilson

  DOI：10.1063/1.1730543

  日期：1959.10

  The microwave spectra of eight isotopic species of acetyl cyanide have been investigated in the region 8000 to 34 000 Mc. The hindered internal rotation of the methyl group splits some of the rotational lines into doublets. Analysis of these splittings for four isotopic species gives a barrier to internal rotation of 1270±30 cal/mole. From the rotational constants of CH3COCN, C13H3COCN, CH3COC13N, CH3CO18CN, CD3COCN, and CD3C13OCN the following structural parameters were determined: C–H1.086±0.005 A∠HCH108∘44′±30′C=O1.226±0.005∠CmethylCO124∘3′±1∘C≡N1.164±0.005∠CCC114∘59′±1∘Cmethyl–Ccarbonyl1.490±0.010∠CCN180∘ (assumed)Ccarbonyl–Ccyanide1.466±0.010.A study of CH2DCOCN and CHD2COCN shows that in its equilibrium configuration, the acetyl cyanide molecule has a methyl hydrogen opposite the oxygen atom. A dipole moment of 3.45D was obtained from Stark effect measurements.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: C: MVol.C4, 6.1.3, page 123 - 125
  作者：

  DOI：——

  日期：——
• Langseth; Bak, 1947, vol. 24, # 3, p. 13
  作者：Langseth、Bak

  DOI：——

  日期：——