2-[(4-chlorophenyl)thio]-N,N-diethylacetamide | 525575-07-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[(4-chlorophenyl)thio]-N,N-diethylacetamide
• 英文别名: 2-(4-chlorophenyl)sulfanyl-N,N-diethylacetamide
• CAS: 525575-07-9
• 化学式: C₁₂H₁₆ClNOS
• mdl: MFCD05039899
• 分子量: 257.784
• InChiKey: MNUPBVUCSGKLOV-UHFFFAOYSA-N

物化性质

• 沸点：
  367.1±27.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(4-chlorophenyl)thio]-N,N-diethylacetamide 在 selenium(IV) oxide 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 生成 4-Cl-C6H4-SO2CH2C(O)NEt2
  参考文献：
  名称：

  Spectroscopic and theoretical studies of some N,N-diethyl-2-[(4′-substituted)phenylsulfonyl]acetamides

  摘要：

  The analysis of the IR carbonyl band of the N,N-diethyl-2-[(4'-substituted)phenylsulfonyl]acetamides Et(2)NC(O)CH(2)S(O)(2)-C(6)H(4)-Y (Y = OMe 1, Me 2,1-13, Cl 4, Br 5, NO(2) 6) supported by B3LYP/6-31G(d,p) calculations for 3, indicated the existence of three pairs (anti and syn) of cis (c) and gauche (g(1) and g(2)) conformers in the gas phase, being the gauche conformers significantly more stable than the cis ones. The anti geometry is more stable than the syn one, for each pair of cis and gauche conformers. The summing up of the orbital (NBO analysis) and electrostatic interactions justifies quite well the populations and the v(CO) frequencies of the anti and syn pairs of c, g(1) and g(2) conformers. The IR higher carbonyl frequency component whose population is ca. 10%, in CCl(4), may be ascribed to the least stable and most polar cis conformer pair (in the gas phase) and the lower frequency component whose population is ca. 90%, to the summing up of the populations of the two most stable and least polar gauche conformer pairs (g(1) and g(2)) (in the gas phase). The reversal of the cis(c)/gauche (g(1) + g(2)) population ratio observed in chloroform ca. 60% (cis)/40% (gauche) and the occurrence of the most polar cis(c) conformer only, in acetonitrile, strongly suggests the coalescence of the two gauche components in a unique carbonyl band in solution. A further support to this rationalization is given by the single point PCM solvation model performed by HF/6-31G(d,p) method, which showed a progressive increase of the c/(g(1) + g(2)) ratio going from gas to CCl(4), to CHCl(3) and to CH(3)CN. X-ray single crystal analysis of 4 indicates that this compound assumes, in the solid state, the syn-clinal (gauche) conformation with respect to the [O=C-CH(2)-S] moiety, and the most stable anti geometry relative to the [C(O)N(CH(2)CH(3))(2)] fragment. In order to obtain larger energy gain from the crystal packing the molecules of 4 are linked in centrosymmetric dimers through two C-H center dot center dot center dot O interactions (C-H([O-Ph])center dot center dot center dot O([SO2])) forming a step ladder. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.06.051
• 作为产物：
  描述：

  N,N-二乙基-2-溴乙酰胺 、 4-氯苯硫酚 在 sodium 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以66%的产率得到2-[(4-chlorophenyl)thio]-N,N-diethylacetamide
  参考文献：
  名称：

  一些N，N-二乙基-2-[（4'-取代）苯硫基]乙酰胺的构象分析。

  摘要：

  通过νCOIR分析，对一些带有取代基OMe 1，Me 2，H 3，Cl 4，Br 5和NO26的N，N-二乙基-2 [（（4'-取代）苯硫基]乙酰胺进行了构象分析。使用B3LYP / 6-311 ++ G（d，p）和可极化连续体模型（PCM）进行计算，并对1、3和6进行NBO分析，对4进行X射线衍射。计算结果表明在气相中存在两个稳定构象对，即gauche（anti; syn）（最稳定）和顺式（anti; syn）。与1和3的顺式构象的极性相比，gauche构象的极性较小，但对6而言，极性更强。在较低频率下观察到的最强烈的IR羰基双峰组分可归因于3的gauche构象构形g（anti; syn）在n-C6H14中为-6，这与PCM计算得出的gauche和cis相对稳定性和频率一致。类似地，正己烷中1和2的单个IR谱带可归因于gauche构象异构体。PCM计算结果与溶液中化合物的IR数据进行了很

  DOI：

  10.1016/j.saa.2013.06.118

文献信息

• Conformational analysis of some N,N-diethyl-2-[(4′-substituted) phenylthio] acetamides
  作者：Elisângela Vinhato、Paulo R. Olivato、Julio Zukerman-Schpector、Maurizio Dal Colle

  DOI：10.1016/j.saa.2013.06.118

  日期：2013.11

  component observed at the lower frequency can be ascribed to the gauche conformers g(anti; syn) for 3-6 in n-C6H14, which is in agreement with the gauche and cis relative stabilities and frequencies resulting from the PCM calculations. Similarly, the single IR band for 1 and 2 in n-hexane may be attributed to the gauche conformers. The PCM calculations compared well with the IR data for the compounds

  通过νCOIR分析，对一些带有取代基OMe 1，Me 2，H 3，Cl 4，Br 5和NO26的N，N-二乙基-2 [（（4'-取代）苯硫基]乙酰胺进行了构象分析。使用B3LYP / 6-311 ++ G（d，p）和可极化连续体模型（PCM）进行计算，并对1、3和6进行NBO分析，对4进行X射线衍射。计算结果表明在气相中存在两个稳定构象对，即gauche（anti; syn）（最稳定）和顺式（anti; syn）。与1和3的顺式构象的极性相比，gauche构象的极性较小，但对6而言，极性更强。在较低频率下观察到的最强烈的IR羰基双峰组分可归因于3的gauche构象构形g（anti; syn）在n-C6H14中为-6，这与PCM计算得出的gauche和cis相对稳定性和频率一致。类似地，正己烷中1和2的单个IR谱带可归因于gauche构象异构体。PCM计算结果与溶液中化合物的IR数据进行了很
• Spectroscopic and theoretical studies of some N,N-diethyl-2-[(4′-substituted)phenylsulfonyl]acetamides
  作者：Elisângela Vinhato、Paulo R. Olivato、Alessandro Rodrigues、Julio Zukerman-Schpector、Maurizio Dal Colle

  DOI：10.1016/j.molstruc.2011.06.051

  日期：2011.9

  The analysis of the IR carbonyl band of the N,N-diethyl-2-[(4'-substituted)phenylsulfonyl]acetamides Et(2)NC(O)CH(2)S(O)(2)-C(6)H(4)-Y (Y = OMe 1, Me 2,1-13, Cl 4, Br 5, NO(2) 6) supported by B3LYP/6-31G(d,p) calculations for 3, indicated the existence of three pairs (anti and syn) of cis (c) and gauche (g(1) and g(2)) conformers in the gas phase, being the gauche conformers significantly more stable than the cis ones. The anti geometry is more stable than the syn one, for each pair of cis and gauche conformers. The summing up of the orbital (NBO analysis) and electrostatic interactions justifies quite well the populations and the v(CO) frequencies of the anti and syn pairs of c, g(1) and g(2) conformers. The IR higher carbonyl frequency component whose population is ca. 10%, in CCl(4), may be ascribed to the least stable and most polar cis conformer pair (in the gas phase) and the lower frequency component whose population is ca. 90%, to the summing up of the populations of the two most stable and least polar gauche conformer pairs (g(1) and g(2)) (in the gas phase). The reversal of the cis(c)/gauche (g(1) + g(2)) population ratio observed in chloroform ca. 60% (cis)/40% (gauche) and the occurrence of the most polar cis(c) conformer only, in acetonitrile, strongly suggests the coalescence of the two gauche components in a unique carbonyl band in solution. A further support to this rationalization is given by the single point PCM solvation model performed by HF/6-31G(d,p) method, which showed a progressive increase of the c/(g(1) + g(2)) ratio going from gas to CCl(4), to CHCl(3) and to CH(3)CN. X-ray single crystal analysis of 4 indicates that this compound assumes, in the solid state, the syn-clinal (gauche) conformation with respect to the [O=C-CH(2)-S] moiety, and the most stable anti geometry relative to the [C(O)N(CH(2)CH(3))(2)] fragment. In order to obtain larger energy gain from the crystal packing the molecules of 4 are linked in centrosymmetric dimers through two C-H center dot center dot center dot O interactions (C-H([O-Ph])center dot center dot center dot O([SO2])) forming a step ladder. (C) 2011 Elsevier B.V. All rights reserved.