乙胺阳离子 | 56995-77-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 乙胺阳离子
• 英文名称: ethylamine cation
• 英文别名: ethylideneamine; protonated form；ethyliden-iminium cation；Ethylimine；ethylideneazanium
• CAS: 56995-77-8
• 化学式: C₂H₅N*H
• 分子量: 44.0763
• InChiKey: MPAYEWNVIPXRDP-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  3
• 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：
  25.6
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  乙胺阳离子 、 乙胺 50.0 ℃ 、0.0 Pa 条件下， 生成 次乙亚胺 、 ethylammonium
  参考文献：
  名称：

  Xu, Guoying; Herman, Jan A.; Wojcik, Leszek, Canadian Journal of Chemistry, 1990, vol. 68, # 4, p. 570 - 574

  摘要：

  DOI：
• 作为产物：
  描述：

  庚胺 生成 乙胺阳离子
  参考文献：
  名称：

  开链脂肪族铝自由基中具有八元环过渡态的分子内氢原子抽象

  摘要：

  长链脂族气相铵自由基（胺分子离子）中氮的氢提取是通过六元，七元和八元环状过渡态发生的。在八元环氢转移之后，随后的断裂特别容易。

  DOI：

  10.1016/s0040-4039(00)98310-2

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。
• Proton affinities and the site of protonation of enamines in the gas phase
  作者：Mark R. Ellenberger、David A. Dixon、William E. Farneth

  DOI：10.1021/ja00408a017

  日期：1981.9
• Unimolecular reactions of isolated organic ions. The importance of ion-dipole interactions
  作者：Richard D. Bowen、Dudley H. Williams

  DOI：10.1021/ja00528a038

  日期：1980.4
• Unimolecular reactions of the isolated immonium ions CH3CH = NH+C4H9, CH3CH2Ch = NH+C4H9 and (CH3)2C = NH+C4H9
  作者：Richard D. Bowen、Alex. W. Colburn、Peter J. Derrick

  DOI：10.1002/oms.1210251005

  日期：1990.10

  AbstractThe reactions of ten metastable immonium ions of general structure R1R2CNH+C4H9 (R1 = H, R2 = CH3, C2H5; R1 = R2 = CH3) are reported and discussed. Elimination of C4H8 is usually the dominant fragmentation pathway. This process gives rise to a Gaussian metastable peak; it is interpreted in terms of a mechanism involving ion‐neutral complexes containing incipient butyl) cations. Metastable immonium ions ontaining an isobutyl group are unique in undergoing a minor amount of imine (R1R2CNH) loss. This decomposition route, which also produces a Gaussian metastable peak, decreases in importance as the basicity of the imine increases. The correlation between imine loss and the presence of an isobutyl group is rationalized by the rearrangement of the appropriate ion‐neutral complexes in which there are isobutyl cations to the isomeric complexes containing the thermodynamically more stable tert‐butyl cations. A sizeable amount of a third reaction, expulsion of C3H6, is observed for metastable n‐C4H9 +NHCR1R2 ions; in contrast to C4H8 and R1R2CNH loss, C3H6 elimination occurs with a large kinetic energy release (40–48 kJ mol−1) and is evidenced by a dish‐topped metastable peak. This process is explained using a two‐step mechanism involving a 1,5‐hydride shift, followed by cleavage of the resultant secondary open‐chain cations, CH3CH+ CH2CH2NHCHR1R2.
• Site of gas-phase methylation of l-phenyl-2-aminopropane
  作者：Herman Zagppey、Roel H. Fokkens、Steen Ingemann、Nico M. M. Nibbering、Helena Florencio

  DOI：10.1002/oms.1210260610

  日期：1991.6

  AbstractThe regioselectivity of methyl cation transfer from (CH3)2F+, (CH3)2Cl+ and (CH3)3O+ to 1‐phenyl‐2‐aminopropane was studied by Fourier transform ion cyclotron resonance in combination with collision‐induced dissociation and neutralization‐reionization mass spectrometry of the stable [M + CH3]+ ions formed in a chemical ionization source. The (CH3)2F+ ion transfers a methyl cation to the NH2 group and the phenyl ring with almost equal probability. Predominant CH3+ transfer to the NH2 group is observed for the (CH3)2Cl+ ion whereas the (CH3)3O+ ion reacts almost exclusively at the amino group. The preference for methylation at NH2 is discussed in terms of a lower methyl cation affinity of the phenyl ring than of the amino group and the existence of an energy barrier for methylation of the phenyl moiety.