2-diphenylphosphinopicolinamide | 234430-13-8

• 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
• 英文名称: 2-diphenylphosphinopicolinamide
• 英文别名: N-diphenylphosphanylpyridine-3-carboxamide
• CAS: 234430-13-8
• 化学式: C₁₈H₁₅N₂OP
• 分子量: 306.304
• InChiKey: HDGXYXZQOMUKOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-diphenylphosphinopicolinamide 在 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 N-(diphenylphosphineoxide)nicotinamide
  参考文献：
  名称：

  Spectroscopic and structural characterization of O,O′-(diphenylphosphineoxide)amidate and acetylacetonate complexes of pentacoordinate nickel(II)

  摘要：

  Heteroleptic nickel pentacoordinate complexes with the macrocyclic ligands 2,4,4-trimethyl-1,5,9-triazacyclododec-1-ene (Me-3-mcN(3)) or its 9-methyl derivative (Me-4-mcN(3)), as ancillary ligands, and O,O'-(diphenylphosphineoxide) amidate ligands, [RC(O)NP(O)Ph-2] (R = C6H6 (1), C5H4N (2), C4H3S (3)), have been prepared as well as related acetylacetonate derivatives. The complexes have been studied by spectroscopic methods (IR, UV-Vis and H-1 NMR). In acetone solution, the complexes exhibit isotropically shifted H-1 NMR resonances. The full assignment of these resonances has been achieved using one- and two-dimensional H-1 NMR techniques. The single-crystal structures of {(Me-4-mcN(3)) Ni[OP(Ph-2)NC(Tf)O]}[PF6] (9) and {(Me-3-mcN(3))Ni(acac)}[PF6] (10) have been established by X-ray diffraction. (C) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.09.075
• 作为产物：
  描述：

  烟酰胺 、 二苯基氯化膦 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-diphenylphosphinopicolinamide
  参考文献：
  名称：

  New Inorganic Metallacycles and the First Six-Membered Covalent “True” Heterocycle – Oxidation of RC(E)NHPPh2 (E = O or S; R = H2N, Ph, or Py) with O, S, or Se to Give RC(E)NHP(E′)Ph2 (E′ = O, S, Se) and Their Coordination Chemistry

  摘要：

  DOI：

  10.1002/(sici)1099-0682(199909)1999:9<1445::aid-ejic1445>3.0.co;2-s

文献信息

• Synthesis and coordination of 2-diphenylphosphinopicolinamide
  作者：Heather L. Milton、Matthew V. Wheatley、Alexandra M.Z. Slawin、J.Derek Woollins

  DOI：10.1016/j.poly.2004.10.004

  日期：2004.12

  The synthesis and coordination of 2-diphenylphosphinopicolinamide (dpppa 1) is reported. Coordination complexes with Pd, Pt, Ru, Rh, Ir and Au are described. The ligand behaves as a monodentate P donor in complexes such as [PtCl2(dpppa-P-2)], [PdCl(allyl)(dpppa-P)], [RuCl2(p-Cymene)(dpppa-P)], cis-[PtCl2(dpppa-P)(PR3)] and [AuCl(dpppa-P)]. Bidentate P, O coordination was accomplished by reaction of BuLi with [RuCl2(p-Cymene)(dpppa-P)], to give [RuCl(p-Cymene)(dpppa-P,O). P,N donor behaviour was achieved by reaction of a monodentate complex with a halide abstractor [AgBF4] generating [RuCl(p-Cymene)(dpppa-P,N)][ClO4] and [RhCl(eta(5)hCl(eta(5)-C5Me5)(dpppa-P,N)][BF4]. The X-ray structures of dpppa, dpppaO, dpppaS, four monodentate complexes and [RuCl(p-Cymene)(dpppa-P,O) are reported. All of the structures contain intramolecular N-(HN)-N-... hydrogen bonding. (C) 2004 Published by Elsevier Ltd.
• P- versus P,O- coordination in complexes of N-(diphenylphosphino)arylamide ligands ArC(O)NHPPh2 (Ar=3-pyridyl, phenyl). X-ray crystal structures of [RhCl2(η5-C5Me5)L2] and [NiCl(EtOH)L22]·Cl·[NiCl2L22] (L2=C6H5CONHPPh2)
  作者：Pravat Bhattacharyya、Tuan Q. Ly、Alexandra M.Z. Slawin、J. Derek Woollins

  DOI：10.1016/s0277-5387(01)00734-3

  日期：2001.6

  The N-(diphenylphosphino)arylamide ligands 3-NC5H4CONHPPh2 (L-1) and C6H5CONHPPh2 (L-2) function as monodentate p-donors in the complexes [RhCl2(eta (5)-C5Me5)L], [RuCl2(eta (6)-p-cymene)L] and cis-[PtCl2L2], as exemplified by the X-ray crystallographically determined structure of [RhCl2(eta (5)-C5Me5)L-2]. For nickel(II), P,O- chelation by L-1,L-2 is exhibited in the bis(bidentate) complexes [NiCl2L2], as demonstrated by the crystal structure of [NiCl(EtOH)L-2(2)]. Cl . [NiCl2L22]; the five-membered Ni-O-C-N-P chelate rings are approximately planar with the phosphorus atoms in the dichloro complex being trans whereas their arrangement is cis in the cation. Comparison of this structure with [RhCl2(eta (5)-C5Me5)L-2] reveals slight elongation of the C=O and P-N lengths upon P,O-chelation of L-2. Solvatochromism for the Ni(II)-L-2 complex (green in ethanol or acetone, brown in chlorinated solvents) arises from solvent-dependent hemilability of the amide oxygen atom, although the L-1 complex of NI(II) is exempt from this behaviour. (C) 2001 Elsevier Science Ltd. All rights reserved.