N,N'-Di-n-butyladipate | 10472-27-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N'-Di-n-butyladipate
• 英文别名: Hexanediamide, N,N'-dibutyl-；N,N'-dibutylhexanediamide
• CAS: 10472-27-2
• 化学式: C₁₄H₂₈N₂O₂
• 分子量: 256.389
• InChiKey: ADUAOVRJMDDTIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为产物：
  描述：

  己二酰氯 、 正丁胺 在 三乙胺 作用下， 以 乙醚 为溶剂， 生成 N,N'-Di-n-butyladipate
  参考文献：
  名称：

  Variable NMR Spin−Lattice Relaxation Times in Secondary Amides:  Effect of Ramachandran Angles on Librational Dynamics

  摘要：

  Deuterium NMR spin-lattice relaxation times (T-1Z) of N-deuterated microcrystalline secondary amides vary from less than 1 s to more than 500 s at room temperature. The main motion effecting relaxation is an out-of-plane libration of the amide, as indicated by temperature-dependent line shapes and anisotropic relaxation spectra. Over 25 amides were measured; they vary with respect to side chain sterics, hydrogen bond lengths, hydrogen bond geometry, and crystal packing, The temperature-dependent deuterium line shape and anisotropic relaxation rates indicate an out-of-plane angular deflection of approximately 10 degrees; the angle is probably similar for the rapidly and slowly relaxing amides, while the apparent time constant for the motion probably varies dramatically. Deuterons in methylene groups on both sides of the amide group for caprylolactam and caprolactam also indicate an out-of-plane libration with relaxation rates faster than that of the amide deuteron, probably because the angular extent of the distortion is greater for the flanking alpha-deuteron than for the amide deuteron. Carbon relaxation measurements on lauryllactam indicate that the whole molecule librates to a comparable extent. Temperature-dependent relaxation rates for caprylolactam and caprolactam showed non-Arrhenius monotonic increases in the relaxation rates with increasing temperature, as expected for libration dynamics; furthermore the quadrupolar relaxation measurements support the assumption that the dominant spectral density contribution is above the Larmor frequency (i.e. T-1Q is longer than T-1Z). In aggregate, the data indicate that the motion effecting amide relaxation is a low-amplitude libration involving the entire molecule. Previous work on the librations of amides suggested that these librations are pronounced on the NMR time scale when the substance is near a phase transition; we report here that there is additionally a relation between the extent of libration and the structure. Comparison of the relaxation times to structures indicates that only amides with flanking alkyl groups on both sides (larger than a methyl group) exhibit extensive libration; furthermore only those amides with both flanking dihedral angles, phi {C2C1-NC(=O)} and psi {N(O=)C-C1'C-2'}, near -60 degrees (similar to+/-40 degrees) have fast spin-lattice relaxation. On the other hand, correlation between the deuterium relaxation times and hydrogen bond length nor geometry nor crystal packing was observed. Variation in the electronic structures of the conjugated amide groups was indirectly probed by measuring the chemical shift anisotropy of the amide carbonyl carbon, the deuterium quadrupolar coupling constant, and vibrational frequencies. These parameters did not vary dramatically, indicating that the electronic structure is not strongly variable; the modest variation did not correlate with deuterium relaxation rates. The chemical shift tensor elements were delta(11) = 91.4 +/- 5, delta(22) = 185 +/- 8, and delta(33) = 245 +/- 3 ppm, the quadrupolar coupling constant and its anisotropy were 203 +/- 10 kHz and 0.15 +/- 0,02, the NH stretch frequency was 3300 +/- 42 cm(-1), and the carbonyl stretch frequency was 1644 +/- 25 cm(-1). We suggest a model in which the shape of the local potential associated with flanking alkyl groups leads to "overdamping" of the amide Librational mode and generates slower (nanosecond) components in the vibrational frequency spectrum.

  DOI：

  10.1021/jp971068c

文献信息

• OBESO R. M.; DE ABAJO J.; FONTAN J., REV. PLAST. MOD. , 1977, 34, NO 257, 679-686
  作者：OBESO R. M.、 DE ABAJO J.、 FONTAN J.

  DOI：——

  日期：——
• US4425161A
  申请人：——

  公开号：US4425161A

  公开（公告）日：1984-01-10
• [EN] METHOD FOR CONVERTING POLYAMIDES INTO NITROGEN-CONTAINING COMPOUNDS<br/>[FR] PROCEDE DE TRANSFORMATION DE POLYAMIDES EN COMPOSES COMPRENANT DE L'AZOTE
  申请人：RHONE-POULENC FIBRES & POLYMERES S.A.

  公开号：WO1997003040A1

  公开（公告）日：1997-01-30

  (EN) A method for converting polyamide compounds including at least two amide functions into simple compounds including nitrogen functions. The method comprises reacting the polyamide compound with a compound including at least one amine function according to reaction A, and reacting the resulting compound (IV) with ammonia according to reaction B. The compound of formula (V) may be hydrogenated to give a diamine.(FR) La présente invention concerne un procédé de transformation de composés polyamides comprenant au moins deux fonctions amides en composés simples comprenant des fonctions azotées. Le procédé de l'invention consiste à faire réagir le composé polyamide avec un composé comprenant au moins une fonction amine selon la réaction A ci-dessus, puis à faire réagir le composé (IV) formé avec de l'ammoniac selon la réaction B. Le composé de formule (V) peut être hydrogéné pour obtenir une diamine.
• Variable NMR Spin−Lattice Relaxation Times in Secondary Amides:  Effect of Ramachandran Angles on Librational Dynamics
  作者：John C. Williams、Ann E. McDermott

  DOI：10.1021/jp971068c

  日期：1998.8.1

  Deuterium NMR spin-lattice relaxation times (T-1Z) of N-deuterated microcrystalline secondary amides vary from less than 1 s to more than 500 s at room temperature. The main motion effecting relaxation is an out-of-plane libration of the amide, as indicated by temperature-dependent line shapes and anisotropic relaxation spectra. Over 25 amides were measured; they vary with respect to side chain sterics, hydrogen bond lengths, hydrogen bond geometry, and crystal packing, The temperature-dependent deuterium line shape and anisotropic relaxation rates indicate an out-of-plane angular deflection of approximately 10 degrees; the angle is probably similar for the rapidly and slowly relaxing amides, while the apparent time constant for the motion probably varies dramatically. Deuterons in methylene groups on both sides of the amide group for caprylolactam and caprolactam also indicate an out-of-plane libration with relaxation rates faster than that of the amide deuteron, probably because the angular extent of the distortion is greater for the flanking alpha-deuteron than for the amide deuteron. Carbon relaxation measurements on lauryllactam indicate that the whole molecule librates to a comparable extent. Temperature-dependent relaxation rates for caprylolactam and caprolactam showed non-Arrhenius monotonic increases in the relaxation rates with increasing temperature, as expected for libration dynamics; furthermore the quadrupolar relaxation measurements support the assumption that the dominant spectral density contribution is above the Larmor frequency (i.e. T-1Q is longer than T-1Z). In aggregate, the data indicate that the motion effecting amide relaxation is a low-amplitude libration involving the entire molecule. Previous work on the librations of amides suggested that these librations are pronounced on the NMR time scale when the substance is near a phase transition; we report here that there is additionally a relation between the extent of libration and the structure. Comparison of the relaxation times to structures indicates that only amides with flanking alkyl groups on both sides (larger than a methyl group) exhibit extensive libration; furthermore only those amides with both flanking dihedral angles, phi C2C1-NC(=O)} and psi N(O=)C-C1'C-2'}, near -60 degrees (similar to+/-40 degrees) have fast spin-lattice relaxation. On the other hand, correlation between the deuterium relaxation times and hydrogen bond length nor geometry nor crystal packing was observed. Variation in the electronic structures of the conjugated amide groups was indirectly probed by measuring the chemical shift anisotropy of the amide carbonyl carbon, the deuterium quadrupolar coupling constant, and vibrational frequencies. These parameters did not vary dramatically, indicating that the electronic structure is not strongly variable; the modest variation did not correlate with deuterium relaxation rates. The chemical shift tensor elements were delta(11) = 91.4 +/- 5, delta(22) = 185 +/- 8, and delta(33) = 245 +/- 3 ppm, the quadrupolar coupling constant and its anisotropy were 203 +/- 10 kHz and 0.15 +/- 0,02, the NH stretch frequency was 3300 +/- 42 cm(-1), and the carbonyl stretch frequency was 1644 +/- 25 cm(-1). We suggest a model in which the shape of the local potential associated with flanking alkyl groups leads to "overdamping" of the amide Librational mode and generates slower (nanosecond) components in the vibrational frequency spectrum.