N-十六烷基-3-(氨基羰基)吡啶碘化物 | 36846-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: N-十六烷基-3-(氨基羰基)吡啶碘化物
• 英文名称: N-hexadecyl-3-(aminocarbonyl)pyridinium iodide
• 英文别名: 1-hexadecylnicotinamide iodide；3-carbamoyl-1-hexadecyl-pyridinium; iodide；3-Carbamoyl-1-hexadecyl-pyridinium; Jodid；1-Hexadecylpyridin-1-ium-3-carboxamide;iodide
• CAS: 36846-92-1
• 化学式: C₂₂H₃₉N₂O*I
• 分子量: 474.469
• InChiKey: NXYPEWYDLPKANM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  26
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-十六烷基-3-(氨基羰基)吡啶碘化物 在 Dowex 1-X₈ anion exchange resin 作用下， 以 乙醇 、 水 为溶剂， 以62%的产率得到N-hexadecyl-3-(aminocarbonyl)pyridinium chloride
  参考文献：
  名称：

  Mechanisms of transmembrane electron transfer: diffusion of uncharged redox forms of viologen, 4,4'-bipyridine, and nicotinamide with long alkyl chains

  摘要：

  Transmembrane electron transfer in lecithin (phosphatidylcholine) vesicles was studied by pulse radiolysis. Upon reduction, cetylmethylviologen (N-hexadecyl-N'-methyl-4,4'-bipyridinium CMV), cetylbipyridine (4-(N-hexadecylpyridinium-4-yl)pyridine, CB), and cetylnicotinamide (N-hexadecyl-3-(aminocarbonyl)pyridinium, CNA) transferred electrons from the bulk water phase to Fe(CN)63- in the internal water phase of the vesicles. The transmembrane electron transfer was found in all cases to proceed through diffusion of uncharged forms of the redox mediators (CMV0, CB0, and CNA0, respectively) but the kinetic behavior varied considerably. The mechanisms for CB and CNA were simple, the reaction following first-order kinetics, and the transmembrane diffusion was rate limiting (k = (1.5 +/- 0.3) x 10(3) S-1 for CB and k = 3.2 +/- 0.5 s-1 for CNA). The mechanism for CMV was more complicated, and the reaction followed second-order kinetics. The rate-determining step was proposed to be the disproportionation of two viologen radicals formed by the radiation pulse (2CMV+ double-line arrow pointing left and right CMV0 + CMV2+), followed by rapid transmembrane diffusion of CMVO and its subsequent reoxidation by Fe(CN)63-. In pulse radiolysis, and in phosphorescence quenching experiments with Pt2(P2O5)4H84-, CB0 and CB+ were used as models in order to obtain the rates of transmembrane diffusion of CMV0 and CMV+, respectively. Our results exclude the possibility of electron tunneling between viologens on opposite sides of the membrane, and they provide strong arguments against transmembrane diffusion of viologen radical (CMV+).

  DOI：

  10.1021/j100141a031
• 作为产物：
  描述：

  碘十六烷 、 烟酰胺 以 乙醇 、 甲苯 为溶剂， 反应 72.0h， 以29%的产率得到N-十六烷基-3-(氨基羰基)吡啶碘化物
  参考文献：
  名称：

  Mechanisms of transmembrane electron transfer: diffusion of uncharged redox forms of viologen, 4,4'-bipyridine, and nicotinamide with long alkyl chains

  摘要：

  Transmembrane electron transfer in lecithin (phosphatidylcholine) vesicles was studied by pulse radiolysis. Upon reduction, cetylmethylviologen (N-hexadecyl-N'-methyl-4,4'-bipyridinium CMV), cetylbipyridine (4-(N-hexadecylpyridinium-4-yl)pyridine, CB), and cetylnicotinamide (N-hexadecyl-3-(aminocarbonyl)pyridinium, CNA) transferred electrons from the bulk water phase to Fe(CN)63- in the internal water phase of the vesicles. The transmembrane electron transfer was found in all cases to proceed through diffusion of uncharged forms of the redox mediators (CMV0, CB0, and CNA0, respectively) but the kinetic behavior varied considerably. The mechanisms for CB and CNA were simple, the reaction following first-order kinetics, and the transmembrane diffusion was rate limiting (k = (1.5 +/- 0.3) x 10(3) S-1 for CB and k = 3.2 +/- 0.5 s-1 for CNA). The mechanism for CMV was more complicated, and the reaction followed second-order kinetics. The rate-determining step was proposed to be the disproportionation of two viologen radicals formed by the radiation pulse (2CMV+ double-line arrow pointing left and right CMV0 + CMV2+), followed by rapid transmembrane diffusion of CMVO and its subsequent reoxidation by Fe(CN)63-. In pulse radiolysis, and in phosphorescence quenching experiments with Pt2(P2O5)4H84-, CB0 and CB+ were used as models in order to obtain the rates of transmembrane diffusion of CMV0 and CMV+, respectively. Our results exclude the possibility of electron tunneling between viologens on opposite sides of the membrane, and they provide strong arguments against transmembrane diffusion of viologen radical (CMV+).

  DOI：

  10.1021/j100141a031

文献信息

• Coenzyme models. Part 35. Charge separation on the micelle surface as a strategy to prove the multi-step reaction mechanism in NADH model reductions
  作者：Seiji Shinkai、Takaharu Tsuno、Yukiko Asatani、Osamu Manabe

  DOI：10.1039/p29830001533

  日期：——

  We have found that (i) the reaction of NADH model compounds with potassium persulphate (PPS) in anionic and non-ionic micelles initiates radical polymerisation of acrylamide and (ii) that reductive desulphonation of 2,4,6-trinitrobenzenesulphonate and 4-carboxy-2,6-dinitrobenzenesulphonate by NADH model compounds in deuterium oxide in the presence of the micelles gives 1,3,5-trinitrobenzene and 3,5-dinitrobenzoic

  我们发现（i）NADH模型化合物与过硫酸钾（PPS）在阴离子和非离子胶束中的反应引发丙烯酰胺的自由基聚合，以及（ii）2,4,6-三硝基苯磺酸盐和4-羧基的还原性脱磺酸作用在胶束存在下，NADH模型化合物在氘化氢中的-2,6-二硝基苯磺酸盐分别得到1,3,5-三硝基苯和3,5-二硝基苯甲酸，它们含有3-16％的氘。结果表明，反应通过自由基离子对中间体的多步氢转移而进行，并且胶束能够离解自由基离子对。
• Zienty, Journal of the American Pharmaceutical Association (1912), 1948, vol. 37, p. 99
  作者：Zienty

  DOI：——

  日期：——