acetylene | 22816-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: acetylene
• 英文别名: 1,2-dideuterio(1,2-13C2)ethyne
• CAS: 22816-36-0
• 化学式: C₂H₂
• 分子量: 30.0
• InChiKey: HSFWRNGVRCDJHI-NJBINRJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  acetylene 在 氢溴酸 作用下， 生成 1,2-dibromoethane-13C2-1,2-d2
  参考文献：
  名称：

  环丙烷-1,2-d2 和环丙烷-1-13C-1,2,3-d3 的外消旋和两种手性形式的合成

  摘要：

  环丙烷-1,2-d 2 和环丙烷-1-13 C-1,2,3-d 3 的外消旋和手性形式已通过基于反式-1,2-双（甲氧基羰基）环丙烷的序列有效制备. 这些二酯已制备成外消旋形式，带有 1,2-d 2 标记和 3- 13 C-1,2,3-d 3 标记。标记的二酯已被拆分以提供两种手性形式，并且外消旋或拆分的二酯已通过涉及还原和脱羰的两步序列转化为相应的特定标记的外消旋或手性环丙烷

  DOI：

  10.1021/ja00050a020
• 作为产物：
  描述：

  在 重水 作用下， 反应 2.0h， 生成 acetylene
  参考文献：
  名称：

  环丙烷-1,2-d2 和环丙烷-1-13C-1,2,3-d3 的外消旋和两种手性形式的合成

  摘要：

  环丙烷-1,2-d 2 和环丙烷-1-13 C-1,2,3-d 3 的外消旋和手性形式已通过基于反式-1,2-双（甲氧基羰基）环丙烷的序列有效制备. 这些二酯已制备成外消旋形式，带有 1,2-d 2 标记和 3- 13 C-1,2,3-d 3 标记。标记的二酯已被拆分以提供两种手性形式，并且外消旋或拆分的二酯已通过涉及还原和脱羰的两步序列转化为相应的特定标记的外消旋或手性环丙烷

  DOI：

  10.1021/ja00050a020

文献信息

• Gas-phase reactions of tantalum carbide cluster ions with deuterium and small hydrocarbons
  作者：Carolyn J. Cassady、Stephen W. McElvany

  DOI：10.1021/ja00168a025

  日期：1990.6

  gas-phase ion/molecule reactions of tantalum carbide cluster ions (TaCsub y}sup +}, y = 0-14) with Dsub 2}, CHsub 4}, Csub 2}Hsub 4}, and Csub 2}Hsub 6} have been investigated by Fourier transform mass spectrometry. Product branching ratios and reaction rate constants are reported. The addition of tantalum dramatically alters the reactivity relative to that of the corresponding carbon clusters (Csub

  碳化钽簇离子(TaCsub y}sup +}, y = 0-14)与Dsub 2}, CHsub 4}, Csub 2}H的气相离子/分子反应sub 4} 和 Csub 2}Hsub 6} 已经通过傅里叶变换质谱法进行了研究。报告了产物支化率和反应速率常数。相对于相应碳簇 (Csub y}sup +}) 的反应性，钽的添加显着改变了反应性，从而得出结论：TaCsub y}sup +} 反应是在金属上引发的。此外，对于 TaCsub y}sup +}，观察到表征 Tasup +} 与烃反应的广泛脱氢和二次反应性。进行了同位素标记前体的实验，以及主要反应产物的低能碰撞诱导解离研究。讨论了这些研究对 TaCsub y}sup +} 结构和反应机制的影响。在 TaCsub y}sup +} 与 sup 13}CHsub 4} 的反应过程中发生了标记碳的总加扰。
• Experimental and Computational Study of the Transformation of Terminal Alkynes to Vinylidene Ligands on <i>trans</i>-(Chloro)bis(phosphine)Rh Fragments and Effects of Phosphine Substituents
  作者：Douglas B. Grotjahn、Xi Zeng、Andrew L. Cooksy、W. Scott Kassel、Antonio G. DiPasquale、Lev. N. Zakharov、Arnold L. Rheingold

  DOI：10.1021/om700355r

  日期：2007.7.1

  the two-dimensional reaction surface, combined density functional/molecular mechanics calculations predict that η2-(C,H) alkyne complex 3 is in a fast equilibrium with the lower energy hydrido(alkynyl) complex 4, and neither species is expected to be present at observable concentrations. Eyring model estimates of the rate constants from these computational data predict the available experimental values

  实验和计算证据表明标题Rh（I）金属片段上末端炔的单分子转化。在双交叉实验中缺乏同位素加扰与先前提出的双分子途径不一致。着眼于单分子流形，炔与金属的结合形成Rh（I）炔π-络合物2，其异构化为Rh（III）氢化（炔基）物种4，最终导致Rh（I）亚乙烯基产物5。在制备不含炔烃的前体时，使用杂环配体（i -Pr）2 PIm'（1b，Im'= 1-甲基-4-叔丁基咪唑-2-基）导致形成物种8具有不稳定的P，N螯合物，而几何上相似的邻甲苯基配体在甲基处发生金属化，因此不适合进行炔烃转化研究。比较动力学研究1B和（我-Pr）2 PPH（1C）所允许的炔结合事件和的转换确定速率常数的2至5（后者，ķ 2 - 5，速度更快9.6倍为1B）。基于二维反应表面的扫描，组合密度泛函/分子力学计算预测，η 2 - （C，H）炔复杂3与较低能量的氢化（炔基）配合物4处于快速平衡状态，并且预计没有两种物质以可观察到
• Contrasting free energies of electron transfer from [6]- and [8]annulenes to their perdeuteriated and per-13C analogs
  作者：Cheryl D. Stevenson、Steven J. Peters、Kerry A. Reidy、Richard C. Reiter

  DOI：10.1021/jo00032a049

  日期：1992.3.1

  A very large equilibrium isotope effect (confirmed via physical separation of the isotopes involved) was observed via the EPR analysis of a mixture of benzene and perdeuteriated-per-C-13-benzene competing for a deficient number of electrons in tetrahydrofuran (THF) in the presence of 18-crown-6 (18C6). The K(eq) for the reaction C6H6.-,K+(18C6) + (C6D6)-C-13 = C6H6 + (C6D6)-C-13.-,K+(18C6) is 0.096 +/- 0.008 at -100-degrees-C. An analogous competition for electrons exists between [8]annulene and perdeuteriated-per-C-13-[8]annulene. In contrast to the benzene system the K(eq) for the reaction C8H8.-,Na+ + (C8D8)-C-13 = C8H8 + (C8D8)-C-13.-,Na+ in liquid ammonia is 1.20 +/- 0.04 at -100-degrees-C. Similar contrasting results (but smaller in magnitude) were observed for the benzene and cyclooctatetraene perdeuteriated and per-C-13 systems. The results are interpreted in terms of the divergence of the [6]annulene system from aromatic character upon electron addition and the convergence of the [8]annulene system toward aromatic character upon electron addition.
• Kinetics and Mechanism of the Formation of the Bis(ethylidyne) Tricobalt Cluster Cp*3Co3(.mu.3-CCH3)2 from Reaction of Acetylene with Cp*3Co3(.mu.2-H)3(.mu.3-H)
  作者：Charles P. Casey、Susan L. Hallenbeck、Ross A. Widenhoefer

  DOI：10.1021/ja00121a018

  日期：1995.4

  The paramagnetic tetrahydride cluster Cp*Co-3(3)(mu(2)-H)(3)(mu(3)-H) (1) reacts with acetylene to ultimately form the bis(ethylidyne) cluster Cp*Co-3(3)(mu(3)-CCH3)(2) (2). Two kinetically formed intermediates were isolated from the reaction: the diamagnetic mono(ethylidyne) trihydride cluster Cp*Co-3(3)(mu(2)-H)(3)(mu(3)-CCH3) (3) and the paramagnetic mono(ethylidyne) monohydride cluster Cp*Co-3(3)(mu(3)-H)(mu(3)-CCH3) (4) Cluster 3 loses H-2 at 80 degrees C [Delta G(double dagger) = 29.5(1) kcal mol(-1)] to generate 4, and 4 reacts with H-2 at 80 degrees C [Delta G(double dagger) = 23.8(1) kcal mol(-1)] to regenerate 3. A third intermediate in the reaction of 1 with acetylene, the bridging acetylene dihydride cluster Cp*Co-3(3)(mu-H)(2)(mu(3)-eta(2)-HCCH) (5), was detected by H-1 NMR spectroscopy at 23 degrees C and rearranges to form exclusively cluster 4. Cluster 1 reacts with DC=CD at 80 degrees C to form Cp*Co-3(3)(mu(2)-H)(2)(mu(2)-D)(mu(3)-CCH2D) (3-CH2D) as the exclusive diamagnetic product. The formation of 3-CH2D is consistent with the presence of the ethylidene dihydride intermediate Cp*Co-3(3)(mu(2)-H)(2)(mu(2)-CDCH2D) (III).
• Cryochemical studies. 3. ESR studies of the reaction of Group IB metal atoms with acetylene and phenylacetylene in a rotating cryostat
  作者：J. H. B. Chenier、J. A. Howard、B. Mile、R. Sutcliffe

  DOI：10.1021/ja00342a023

  日期：1983.2