Elusive forms and structures of N-hydroxyphthalimide:: The colorless and yellow crystal forms of N-hydroxyphthalimide

被引:8
作者
Reichelt, Hendrik [1 ]
Faunce, Chester A. [1 ]
Paradies, Henrich H. [1 ]
机构
[1] Univ Salford, Mat Res Inst, Joule Phys Lab, Salford M5 4WT, Lancs, England
关键词
D O I
10.1021/jp068599y
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A comprehensive structural characterization of the colorless and yellow forms of N-hydroxyphthalimide (NHP), the deuterated form (NDP), and the ethoxylated form (ethoxy-NHP) has been carried out using single-crystal X-ray diffraction, FTIR and Raman spectroscopies, and scanning electron microscopy. Both NHP and NDP forms crystallize in the monoclinic space group (P2(1)/c, No. 14). The various forms of NHP differ in the way in which the molecules adjoin one another through their N-hydroxyl groups and how the carbonyls of the isoindole-1,3-dione ring differ through intermolecular hydrogen bonding. Although the hydrogen bonding about the b axis is virtually the same, the isoindole-1,3-dione ring experiences different twists for the two NHP forms. Both the colorless and yellow forms of NHP exhibit strong intermolecular hydrogen bonding between O(3) and H(1). In the yellow form, the N-hydroxyl group is significantly out of the plane (similar to 1.19 degrees), but the N-hydroxyl group in the colorless form is only similar to 0.06 degrees out of the plane. Both forms of NHP reveal an infinite chain of intermolecular hydrogen-bonded molecules in the direction of the b axis; however, the molecules are ordered differently within the unit cells. The hydrogen-bond geometry for the yellow form of NHP is O(2)-H(1)center dot center dot center dot O(3), with an angle of 185 degrees, intermolecular distances of O(2)center dot center dot center dot O(3) = 2.68 A and H(1)center dot center dot center dot O(3) = 1.70 A, and an intramolecular hydrogen bond of O(1)center dot center dot center dot H(1) = 1.17 A. The colorless form of NHP shows an intermolecular hydrogen-bond geometry between O(3) and H(1) with a distance of 1.78 A; the O(2)-O(3) distance is 2.71 A. The O(2)-H(1)center dot center dot center dot O(3) angle is 159 degrees, and the intramolecular distance is O(1)center dot center dot center dot H(1) = 0.97 A. The N-ethoxy derivative of NHP crystallizes in an orthorhombic space group (Pnma, No. 62) and exhibits no hydrogen bonding, displaying a strong head-to-tail stacking of the planar rings along the needle axis direction.
引用
收藏
页码:2587 / 2601
页数:15
相关论文
共 50 条
  • [31] Pullulan Oxidation in the Presence of Hydrogen Peroxide and N-Hydroxyphthalimide
    Biliuta, Gabriela
    Baron, Raluca Ioana
    Coseri, Sergiu
    MATERIALS, 2022, 15 (17)
  • [32] Aerobic oxidation with N-hydroxyphthalimide catalysts in ionic liquid
    Wang, JR
    Liu, L
    Wang, YF
    Zhang, Y
    Deng, W
    Guo, QX
    TETRAHEDRON LETTERS, 2005, 46 (27) : 4647 - 4651
  • [33] N-Hydroxyphthalimide: What Else Can You Ask For?
    Alvarez, Leonardo X.
    SYNLETT, 2011, (01) : 141 - 142
  • [34] Ring opening of N-hydroxyphthalimide to construct phenylurea derivatives
    Wu, Yinhui
    Lv, Bin
    Zhang, Yanan
    Gao, Pan
    Zhang, Min
    Yuan, Yu
    SYNTHETIC COMMUNICATIONS, 2021, 51 (13) : 2025 - 2033
  • [35] Advances of N-Hydroxyphthalimide Esters in Photocatalytic Alkylation Reactions
    He Shuaiqi
    Li Haocong
    Chen Xiaolan
    Krylov, Igor B.
    Terent'ev, Alexander O.
    Qu Lingbo
    Yu Bing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (12) : 4661 - 4689
  • [36] PRIMARY ALKOXYLAMINES .1. SYNTHESIS FROM N-HYDROXYPHTHALIMIDE
    ROUGNY, A
    DAUDON, M
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE PARTIE II-CHIMIE MOLECULAIRE ORGANIQUE ET BIOLOGIQUE, 1976, (5-6): : 833 - 838
  • [37] Aerobic oxidation reactions catalyzed by N-hydroxyphthalimide and its analogues
    Xu Haifeng
    Tang Ruiren
    Gong Nianhua
    Liu Changhui
    Zhou Yaping
    PROGRESS IN CHEMISTRY, 2007, 19 (11) : 1736 - 1745
  • [38] Electrochemically promoted decarboxylative borylation of alkyl N-hydroxyphthalimide esters
    Jian-Jun Dai
    Xin-Xin Teng
    Wen Fang
    Jun Xu
    Hua-Jian Xu
    ChineseChemicalLetters, 2022, 33 (03) : 1555 - 1558
  • [39] Photoinduced Decarboxylative Thioacylation of N-Hydroxyphthalimide Esters with Tetraalkylthiuram Disulfides
    Wang, Qian
    Zhang, Cheng-Lin
    Li, Yan-Fei
    Zhou, Yu-Jing
    Cui, Fei-Hu
    Jiang, Jing-Chen
    Pan, Ying-Ming
    Duan, Wen-Gui
    Tang, Hai-Tao
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (68)
  • [40] Mechanisms for radical reactions initiating from N-hydroxyphthalimide esters
    Azpilcueta-Nicolas, Carlos R.
    Lumb, Jean-Philip
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 346 - 378