N-(diethylaminothiocarbonyl)-N'-monoethylbenzamidine | 90473-92-0

• 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: N-(diethylaminothiocarbonyl)-N'-monoethylbenzamidine
• 英文别名: N-(Diethylcarbamothioyl)-N'-ethylbenzenecarboximidamide；1,1-diethyl-3-(N-ethyl-C-phenylcarbonimidoyl)thiourea
• CAS: 90473-92-0
• 化学式: C₁₄H₂₁N₃S
• 分子量: 263.407
• InChiKey: VSKAFSDTWNSPRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  bis(N',N'-diethyl-N-benzoylthioureato)nickel(II) 在 氯化亚砜 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 N-(diethylaminothiocarbonyl)-N'-monoethylbenzamidine
  参考文献：
  名称：

  Structure and solid–liquid phase transition thermodynamics of N-(diethylaminothiocarbonyl)benzimido derivatives

  摘要：

  A set of three N-(diethylaminothiocarbonyl)benzimido derivatives was structurally characterized by solid state single crystal X-ray diffractometry. The temperature, standard molar enthalpies, and entropies of fusion were measured and derived using differential scanning calorimetry, including two more derivatives, whose structures have been published before. The compounds were further analysed by solid state FIR spectroscopy and the experimental FTIR spectra were compared with the calculated gas phase spectra at the B3LYP/6-311+G(d) level of theory. The structural results for the set were further used in the interpretation of thermophysical phase transition properties of the title compounds. A detailed molecular picture of N-(diethylaminothiocarbonyl)benzimido derivatives was obtained from Natural Bond Order (NBO) analysis. The combination of the applied methods reveals a deeper insight into the structures of this type of compound. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.08.014

文献信息

• Reaktionen an nickel(II)koordinierten N-Acylthioharnstoffen mit Säurechloriden: ein einfacher zugang für neue Thioharnstoff-derivate
  作者：L. Beyer、J. Hartung、R. Widera

  DOI：10.1016/s0040-4020(01)91188-3

  日期：1984.1

  The reaction of transition metal coordinated N,N-dialkylsubstituted N'-benzoyl thioureas with electrophilic agents differs from the reaction of the non-coordinated ligands. The nickel(II)chelates 1 form with organic acid chlorides RCOCI the N',N'-diacylated thioureas 2 and with thionyl chloride the n-(amino-thiocarbonyl)benzimide chlorides 3. The substitution of the chlorine in 3 yields new derivatives

  过渡金属配位的N，N-二烷基取代的N'-苯甲酰基硫脲与亲电子试剂的反应不同于非配位的配体的反应。镍（II）螯合物1种形式与有机酸氯化物RCOCI的N“ N” -diacylated硫脲2，并用亚硫酰氯Ñ - （氨基硫代羰基）苯甲亚胺氯化物3。的氯的取代3个产率的硫脲衍生物的新：由醇化物的反应Ñ -aminothiocarbony）benzimidates 4形成，与氨和与胺，ñ - （氨基硫代）苄脒形成5，并用硫化钠形成N-（硫代苯甲酰基）硫脲6。产物的结构通过1 H-NMR光谱，X射线光电子能谱（ESCA）和质谱来描述。
• BEYER, L.;HARTUNG, J.;WIDERA, R., TETRAHEDRON, 1984, 40, N 2, 405-412
  作者：BEYER, L.、HARTUNG, J.、WIDERA, R.

  DOI：——

  日期：——
• Thermochemical studies of two N-(diethylaminothiocarbonyl)benzimido derivatives
  作者：Manuel A.V. Ribeiro da Silva、Luís M.N.B.F. Santos、Bernd Schröder

  DOI：10.1016/j.jct.2006.01.006

  日期：2006.11

  The standard (p degrees = 0.1 MPa) molar energies of combustion in oxygen of N-(diethylaminothiocarbonyl)-N'-monoethylbenzamidine, PhCNHEtNCSNEt2 (DATMB), and N-(diethylaminothiocarbonyl)benzimido ethylester, PhCOEtNCSNEt2 (DATBE), were measured, at T = 298.15 K, by rotating-bomb calorimetry. The standard molar enthalpies of sublimation of these compounds were determined using Calvet microcalorimetry. These values were used to derive the standard molar enthalpies of formation of the title compounds, in their crystalline and gaseous phases, respectively.Compounds -Delta U-c degrees(m) (cr)/ -Delta H-f degrees(m)(cr)/ Delta H-g(cr)degrees(m)/ (kJ center dot mol(-1)) (kJ center dot mol(-1)) (kL center dot mol(-1))N-(Diethylaminothiocarbonyl)-N'-monoethylbenzamidine (DATMB) 9053.6 +/- 3.9 45.7 +/- 4.4 141.2 +/- 1.2N-(Diethylaminothiocarbonyl)benzimido ethylester (DATBE) 8780.9 +/- 4.0 176.2 +/- 4.4 135.6 +/- 2.6The standard molar enthalpies of formation for the two title compounds, in the gaseous state, were also calculated based on density functional theory at the B3LYP/6-311++G(2dfp)//6-31+G(d,p)-level of theory, anchored on previous experimental data for the standard molar enthalpy of formation of N-(diethylaminothiocarbonyl)-benzamidine. (c) 2006 Elsevier Ltd. All rights reserved.
• Structure and solid–liquid phase transition thermodynamics of N-(diethylaminothiocarbonyl)benzimido derivatives
  作者：Bernd Schröder、Ligia R. Gomes、John Nicolson Low、Luís M.N.B.F. Santos、Ana S.M.C. Rodrigues

  DOI：10.1016/j.molstruc.2011.08.014

  日期：2011.10

  A set of three N-(diethylaminothiocarbonyl)benzimido derivatives was structurally characterized by solid state single crystal X-ray diffractometry. The temperature, standard molar enthalpies, and entropies of fusion were measured and derived using differential scanning calorimetry, including two more derivatives, whose structures have been published before. The compounds were further analysed by solid state FIR spectroscopy and the experimental FTIR spectra were compared with the calculated gas phase spectra at the B3LYP/6-311+G(d) level of theory. The structural results for the set were further used in the interpretation of thermophysical phase transition properties of the title compounds. A detailed molecular picture of N-(diethylaminothiocarbonyl)benzimido derivatives was obtained from Natural Bond Order (NBO) analysis. The combination of the applied methods reveals a deeper insight into the structures of this type of compound. (C) 2011 Elsevier B.V. All rights reserved.