urotropine and 4-hydroxybenzoic acid complex

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: urotropine and 4-hydroxybenzoic acid complex
• 英文别名: 4-Hydroxybenzoic acid;1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane
• 化学式: C₆H₁₂N₄*C₇H₆O₃
• 分子量: 278.311
• InChiKey: HBEOOOAZSRLJFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  70.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  乌洛托品 、 对羟基苯甲酸 以 甲醇 、 乙酸乙酯 为溶剂， 生成 urotropine and 4-hydroxybenzoic acid complex
  参考文献：
  名称：

  Salts of hexamethylenetetramine with organic acids: Enhanced anomeric interactions with a lowering of molecular symmetry revealed by crystal structures

  摘要：

  The hexamethylenetetramine (HMT) framework displays interesting stereoelectronic interactions of the anomeric type. In the highly symmetrical parent system, the nitrogen centres act as both donors and acceptors. Protonation lowers symmetry and also leads to an enhancement of the anomeric interaction around the protonated centre. X-ray diffraction crystal structures of four derivatives of HMT - with succinic, (DL)-malic, phthalic and 4-hydroxybenzoic acids - reveal significant trends. (The first three form well-defined salts, 4-hydroxybenzoic acid forming a co-crystalline compound.) Each molecular structure is essentially characterised by a major anomeric interaction involving the protonated centre as acceptor. In two cases (succinic and 4-hydroxybenzoic), secondary protonation leads to a weaker anomeric interaction site that apparently competes with the dominant one. Bond length changes indicate that the anomeric interaction decreases as malic > phthalic > succinic > 4-hydroxybenzoic, which correlates with the degree of proton transfer to the nitrogen centre. Along with other bond length and angle changes, the results offer insight into the applicability of the antiperiplanar lone pair hypothesis (ALPH) in a rigid system. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.11.013

文献信息

• CRYSTALLINE COMPLEXES OF 4-HYDROXY BENZOIC ACID AND SELECTED PESTICIDES
  申请人：BASF SE

  公开号：EP2496077A2

  公开（公告）日：2012-09-12
• Crystalline Complexes of 4-Hydroxy Benzoic Acid and Selected Pesticides
  申请人：Saxell Heidi Emilia

  公开号：US20120220463A1

  公开（公告）日：2012-08-30

  The present invention relates to crystalline complexes of 4-hydroxy benzoic acid and selected pesticides. It also relates to agriculturally useful compositions of the complexes.
• US9173391B2
  申请人：——

  公开号：US9173391B2

  公开（公告）日：2015-11-03
• [EN] CRYSTALLINE COMPLEXES OF 4-HYDROXY BENZOIC ACID AND SELECTED PESTICIDES<br/>[FR] COMPLEXES CRISTALLINS D'ACIDE 4-HYDROXYBENZOÏQUE ET DE PESTICIDES SÉLECTIONNÉS
  申请人：BASF SE

  公开号：WO2011054741A2

  公开（公告）日：2011-05-12

  The present invention relates to crystalline complexes of 4-hydroxy benzoic acid and selected pesticides. It also relates to agriculturally useful compositions of the complexes.
• Salts of hexamethylenetetramine with organic acids: Enhanced anomeric interactions with a lowering of molecular symmetry revealed by crystal structures
  作者：Sosale Chandrasekhar、Somnath Mukherjee

  DOI：10.1016/j.molstruc.2014.11.013

  日期：2015.2

  The hexamethylenetetramine (HMT) framework displays interesting stereoelectronic interactions of the anomeric type. In the highly symmetrical parent system, the nitrogen centres act as both donors and acceptors. Protonation lowers symmetry and also leads to an enhancement of the anomeric interaction around the protonated centre. X-ray diffraction crystal structures of four derivatives of HMT - with succinic, (DL)-malic, phthalic and 4-hydroxybenzoic acids - reveal significant trends. (The first three form well-defined salts, 4-hydroxybenzoic acid forming a co-crystalline compound.) Each molecular structure is essentially characterised by a major anomeric interaction involving the protonated centre as acceptor. In two cases (succinic and 4-hydroxybenzoic), secondary protonation leads to a weaker anomeric interaction site that apparently competes with the dominant one. Bond length changes indicate that the anomeric interaction decreases as malic > phthalic > succinic > 4-hydroxybenzoic, which correlates with the degree of proton transfer to the nitrogen centre. Along with other bond length and angle changes, the results offer insight into the applicability of the antiperiplanar lone pair hypothesis (ALPH) in a rigid system. (C) 2014 Elsevier B.V. All rights reserved.