methyleneimmonium ion | 28963-72-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyleneimmonium ion
• 英文别名: Methaniminium；methylideneazanium
• CAS: 28963-72-6
• 化学式: CH₄N
• 分子量: 30.0495
• InChiKey: WDWDWGRYHDPSDS-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  2
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.6
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  methyleneimmonium ion 在 环己酮 作用下， 生成 亚甲基亚胺
  参考文献：
  名称：

  Thermokinetic Determination of Gas-Phase Basicities. Application to Ketene, Methylketene, and Formaldimine

  摘要：

  Rate constants have been determined for proton transfer reactions of the type [MH](+) + B reversible arrow M + [BH](+), where M is ketene, methylketene, and formaldimine and B is a reference base. A quantitative relationship between the rate constant and the free energy (or enthalpy) of the reaction allows the determination of the gas-phase basicity, GB, (or proton affinity, PA) of M. This thermokinetic method gives results comparable to that obtained from equilibrium constant measurements. The values derived for ketene, methylketene, and formaldimine follow: GB(ketene) = 788 +/- 3 kJ/mol, PA(ketene) = 817 +/- 3 kJ/mol; GB(methylketene) = 809 +/- 3 kJ/mol, PA(methylketene)= 842 +/- 3 kJ/mol; GB(formaldimine) = 830 +/- 3 kJ/mol and PA(formaldimine) = 860 +/- 5 kJ/mol. Heats of formation of methylketene and of formaldimine that may be deduced from a combination of these results with literature data are as follows: Delta H-f degrees(300) (CH3CHCO) = -97 +/- 5 kJ/mol and Delta H-f degrees(300) (CH2=NH) = 75 +/- 5 kJ/mol.

  DOI：

  10.1021/jp960761h
• 作为产物：
  描述：

  甲胺 在 铜 作用下， 生成 methyleneimmonium ion
  参考文献：
  名称：

  CnH2n+2N+ 离子的表观电位 (n = 1-3)

  摘要：

  文献中关于 C/sub n/H/sub 2n+2/N/sup +/ 离子产生的单-、二-和三甲胺的出现电位存在相当大的差异。通过在流管装置中观察母体分子与选定金属离子的反应，确定出现电位的上限和下限。对于 AP(C/sub 2/H/sub 6/N/sup +/) 和 AP(C/sub 3/H/sub 8/N/sup +/)，9.9 /plus minus/ 0.1 eV 是上限并且 9.2 /plus minus/ 0.2 eV 是下限，而 CH/sub 4/N/sup +/ 的值为 9.9 /plus minus/ 0.1 /le/ 10.6 /plus minus/ 0.1 eV。21 个参考文献，4 个表格。

  DOI：

  10.1021/ja00228a012

文献信息

• Trends in alkyl substituent effects on nucleophilic reactions of carbonyl compounds: Gas phase reactions between ammonia and R1R2COCH3+ oxonium ionsElectronic supplementary information (ESI) available: proton affinities, geometries and energies of optimised structures, structures of the stationary points and a plot of experimental and RRKM ln(kae/ksub) against a-stabilisation constants. See http://www.rsc.org/suppdata/ob/b2/b209955c/
  作者：Lihn Bache-Andreassen、Einar Uggerud

  DOI：10.1039/b209955c

  日期：2003.2.11

  The reactivity of carbonyl substituted methyl oxonium ions (R1R2COCH3+) towards ammonia has been investigated using an FT-ICR mass spectrometer and ab initio calculations. The monosubstituted ions (R1 = H; R2 = H, CH3, C2H5 and i-C3H7) show different reaction patterns with variable degree of: (1) nucleophilic substitution, (2) addition-elimination and (3) proton transfer, when reacted with ammonia

  已使用FT-ICR质谱仪和从头算计算研究了羰基取代的甲基氧鎓离子（R1R2COCH3 +）对氨的反应性。单取代离子（R1 = H; R2 = H，CH3，C2H5和i-C3H7）显示不同的反应模式，并具有不同程度的变化：（1）亲核取代，（2）加成消除和（3）质子转移用氨水。在所有情况下，加成消除都超过亲核取代，并且观察到的反应很慢。反应性的趋势与烷基的电子性质一致，如通过单参数线性或轻微非线性模型表示的。
• Rates of hydride abstraction from amines via reactions with ground-state silver(+) and copper(+)
  作者：S. W. Sigsworth、A. W. Castleman

  DOI：10.1021/ja00192a012

  日期：1989.5

  Agsup +} and Cusup +} with mono- (MMA), di- (DMA), and trimethylamine (TMA) were measured. In all cases except Agsup +} with monomethylamine the reactions were found to be fast bimolecular ones. The values are 2.1, 1.7, and 1.5 times} 10sup minus}9} cmsup 3} ssup minus}1} for Cusup +} with MMA, DMA, and TMA, respectively, and 1.6 and 1.4 times}10sup minus}9} cmsup 3}ssup minus}1} for

  测量基态Agsup +} 和Cusup +} 与单- (​​MMA)、二- (DMA) 和三甲胺(TMA) 的反应速率。在除 Agsup +} 与单甲胺之外的所有情况下，发现反应是快速的双分子反应。对于具有 MMA、DMA 和 TMA 的 Cusup +}，这些值分别为 2.1、1.7 和 1.5 times} 10sup minus}9} cmsup 3} ssup minus}1}，并且Agsup +} 与 DMA 和 TMA 分别为 1.6 和 1.4 times}10sup minus}9} cmsup 3}ssup minus}1}。反应的产物是去除了氢原子的胺离子。Agsup +} 与 MMA 反应的双分子通道是吸热的，并且发现缔合复合物是反应的产物。发现观察到的速率与参数化轨迹计算方法的预测相当吻合。
• Reactions of the H_<i>n</i>S⁺ ions (<i>n</i> = 0 to 3) with several molecular gases at thermal energies
  作者：David Smith、Nigel G. Adams、Werner Lindinger

  DOI：10.1063/1.442498

  日期：1981.10

  The rate coefficients and product ion distributions have been determined at room temperature for the reactions of the ions HnS+ (n = 0 to 3) with several diatomic and polyatomic gases. The reactions generally proceed at or near the collisional limit, often generating multiple products. Charge transfer, proton transfer, and atom abstraction, in some cases occurring in parallel, are evident within the data array, emphasizing the complexity of these reactions. The results obtained for the near-thermoneutral reactions of S+ and HS+ with H2S have provided values for the recombination energies of HS+ and H2S+ ions which, within the limitations of the assumptions made, are more closely defined than the previous values.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: S: SVol.4a/b, 5.1.3, page 469 - 471
  作者：

  DOI：——

  日期：——
• A selected ion flow tube study of the reactions of the PH⁺_<i>n</i> ions (<i>n</i>=0 to 4) with several molecular gases at 300 K
  作者：David Smith、Bruce J. McIntosh、Nigel G. Adams

  DOI：10.1063/1.456337

  日期：1989.6

  The reactions of ions in the series PH+n (n=0 to 4) have been studied at 300 K with CH3NH2, PH3, NH3, CH3CCH, H2S, C2H4, CH3OH, COS, C2H2, O2, H2O, CH4, HCN, CO2, CO, and H2 using a selected ion flow tube (SIFT) apparatus. The majority are fast binary reactions, the measured rate coefficients, k, being close to the respective collisional values, and for reactions involving polyatomic reactant molecules multiple product ions are observed. Most reaction mechanisms are represented in this large number of reactions including charge transfer, proton transfer, atom abstraction and especially evident is phosphorus atom insertion in which product ions such as HnPN+, HnPO+, HnPS+ and HnCmP+ are formed. The reactions of the PH+n ions (n=0 to 2) with CO2, CO, and H2 proceed by the process of ternary association except for the P+ reaction with CO2, in which PO+ is formed in a fast binary reaction. PH+4 reacts only with CH3NH2 and NH3 by fast proton transfer, a process which is always rapid when it is exothermic. Upper limits to the heats of formation of HPO+, H2PO+, PC2H2+ and HCP have also been deduced from their observation as products of some of the reactions.