N-carboxymethyl-N,N'-dimethylpiperazinium inner salt | 882005-60-9

• 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: N-carboxymethyl-N,N'-dimethylpiperazinium inner salt
• 英文别名: N,N'-dimethylpiperazine mono-betaine；1,4-dimethylpiperazine monobetaine；2-(1,4-Dimethylpiperazin-1-ium-1-yl)acetate
• CAS: 882005-60-9
• 化学式: C₈H₁₆N₂O₂
• 分子量: 172.227
• InChiKey: TZEXYNXZHVYWSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-carboxymethyl-N,N'-dimethylpiperazinium inner salt 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以62%的产率得到N,N'-dimethylpiperazine monobetaine dihydrochloride
  参考文献：
  名称：

  N,N'-二甲基哌嗪甜菜碱及其氢卤化物的分子结构、氢键、碱性和光谱性质

  摘要：

  摘要 合成了两种 N,N'-二甲基哌嗪甜菜碱（单 (3) 和双 (6)）。甜菜碱 3 与两当量的 HCl 或 HBr 反应，而 6 仅与一当量反应。在通过 X 射线衍射确定的 N,N'-二羧甲基-N,N'-二甲基哌嗪单盐酸盐（N,N'-二甲基哌嗪双甜菜碱单盐酸盐，7-Cl）的晶体结构中，哌嗪鎓部分形成了由非常强的桥接的无限链, 对称和线性氢键 (O⋯O 2.460(2) A)。哌嗪环采用椅子构象，轴向为 CH2COOH 基团，赤道位为甲基。N+ 原子与 Cl- 离子和羧酸根的氧原子发生静电相互作用。7-Cl 的 FTIR 光谱在 1500-400 cm-1 区域显示出强烈的宽吸收，在 1734 cm-1 处有 νCO 波段。3 和 6 的 pKa 值是通过电位滴定确定的。分析了 D2O 中的 1H 和 13C NMR 光谱。

  DOI：

  10.1016/s0022-2860(02)00234-x
• 作为产物：
  描述：

  N-carboethoxymethyl-N,N'-dimethylpiperazinium chloride 在 Amberlite IRA 420 resin 作用下， 以 水 为溶剂， 以97%的产率得到N-carboxymethyl-N,N'-dimethylpiperazinium inner salt
  参考文献：
  名称：

  N,N'-二甲基哌嗪甜菜碱及其氢卤化物的分子结构、氢键、碱性和光谱性质

  摘要：

  摘要 合成了两种 N,N'-二甲基哌嗪甜菜碱（单 (3) 和双 (6)）。甜菜碱 3 与两当量的 HCl 或 HBr 反应，而 6 仅与一当量反应。在通过 X 射线衍射确定的 N,N'-二羧甲基-N,N'-二甲基哌嗪单盐酸盐（N,N'-二甲基哌嗪双甜菜碱单盐酸盐，7-Cl）的晶体结构中，哌嗪鎓部分形成了由非常强的桥接的无限链, 对称和线性氢键 (O⋯O 2.460(2) A)。哌嗪环采用椅子构象，轴向为 CH2COOH 基团，赤道位为甲基。N+ 原子与 Cl- 离子和羧酸根的氧原子发生静电相互作用。7-Cl 的 FTIR 光谱在 1500-400 cm-1 区域显示出强烈的宽吸收，在 1734 cm-1 处有 νCO 波段。3 和 6 的 pKa 值是通过电位滴定确定的。分析了 D2O 中的 1H 和 13C NMR 光谱。

  DOI：

  10.1016/s0022-2860(02)00234-x

文献信息

• Supramolecular structure of the 1:2 complex of 1,4-dimethylpiperazine mono-betaine with squaric acid
  作者：Zofia Dega-Szafran、Andrzej Katrusiak、Anna Komasa、Miroslaw Szafran

  DOI：10.1080/10610278.2013.792342

  日期：2013.7.1

  The 1: 2 complex of 1,4-dimethylpiperazine mono-betaine (MBPZ) with squaric acid (H(2)SQ) has been characterised by single-crystal X-ray analysis, FTIR and NMR spectroscopies, and by DFT calculations. The crystals are monoclinic, space group P2(1)/c. Two MBPZ cations and four hydrogen squarate anions (HSQ(-)) are linked by strong O(1)=H center dot center dot center dot O(13) (2.525(4) angstrom), O(14)-H center dot center dot center dot O(21) (2.511(4) angstrom) and N(4)-H center dot center dot center dot O(23) (2.607(3)angstrom) hydrogen bonds into a cyclamer R-6(6)(38). In turn, the cyclamers are linked into a helix C-4(4)(20) through two O(24)-H center dot center dot center dot O(11) hydrogen bonds of 2.516(4)angstrom. The piperazinium ring has a chair conformation with N(4)-CH3 and N(1)-CH2COOH substituents in the equatorial positions, and N(1)-CH3 in the axial position. The FTIR spectrum is consistent with the crystal data. Two models of the 1: 2 complex of MBPZ with H(2)SQ have been optimised at the B3LYP/6-311++G(d,p) level of theory and have been used to calculate harmonic IR frequencies. One of the models (2) is dominated by electrostatic attraction between NH(4)(+) and HSQ(-), whereas in the other (3) squaric acid interacts with a zwitterionic MBPZ through the O-H center dot center dot center dot O and O-H center dot center dot center dot N hydrogen bonds.
• N,N′-Dimethylpiperazine mono-betaine complex with two molecules of 3-iodobenzoic acid and water studied by X-ray diffraction, DFT, FTIR and NMR methods
  作者：Z. Dega-Szafran、A. Katrusiak、M. Szafran

  DOI：10.1016/j.molstruc.2007.05.044

  日期：2008.3

  N,N'-Dimethylpiperazine mono-betaine (N-carboxymethyl-N,N'-dimethylpiperazinium inner salt, MBPZ) forms a crystalline complex with two molecules of 3-iodobenzoic acid (3IBA). The complex crystallizes as a monohydrate, MBPZ(3IBA)(2)H2O. The complex has been characterized by X-ray diffraction and FTIR, Raman, H-1 and C-13 NMR spectroscopies. The crystals are monoclinic, space group P2(1)/c, with a = 6.7810(17), b = 38.391(4), c = 10.0542(16) angstrom, beta = 90.024(18)degrees. The piperazinium ring has a chair conformation with the N+CH2COO- substituent in the axial and both methyl groups in the equatorial positions. The 3IBA molecules interact with the carboxylate group of N+CH2COO- and N' atom through the O-H center dot center dot center dot O and O-H center dot center dot center dot N hydrogen bonds of the lengths 2.550 and 2.695 angstrom. The water molecules link MBPZ(3IBA)(2) complexes by the O-H center dot center dot center dot OOCCH2N+ hydrogen bonds of 2.850 and 2.793 angstrom into infinite chains. The MBPZ(3XBA)(2)H2O (X = I, Br, Cl), MBPZ(3IBA)(2) complexes and MBPZ have been analyzed by the B3LYP/MidiX level of theory. The conformers with the axial CH2COO- substituent have lower energies than these with the equatorial CH2COO- one. The bands at 3433, 2790, 2450, 1915 cm(-1) assigned to the v(OH) vibration of the various hydrogen bonds, and two bands attributed to the v(C=O) (1680 cm(-1)) and v(as)(COO) (1660 cm(-1)) vibrations in the FTIR spectrum confirm the structure of the title complex. The H-1-C-13 HMBC spectrum has been analyzed in order to assign the carbon-13 chemical shifts. (c) 2007 Elsevier B.V. All rights reserved.