Seven 3D organic salts from 2-(imidazol-1-yl)-1-phenylethanone and acidic components

被引:11
|
作者
Xu, Weiqiang [1 ,4 ]
Lu, Yuan [1 ,2 ]
Xia, YeYu [2 ]
Liu, Bin [1 ,2 ]
Jin, Shouwen [1 ,2 ]
Zhong, Bingwei [1 ]
Wang, Daqi [3 ]
Guo, Ming [2 ]
机构
[1] Zhejiang A&F Univ, Jiyang Coll, Zhuji 311800, Zhejiang, Peoples R China
[2] Zhejiang A&F Univ, Key Lab Chem Utilizat Forestry Biomass Zhejiang P, Linan 311300, Zhejiang, Peoples R China
[3] Liaocheng Univ, Dept Chem, Liaocheng 252059, Shandong, Peoples R China
[4] Zhejiang A&F Univ, Coll Engn, Linan 311300, Peoples R China
关键词
Crystal structure; 3D framework; H-bonds; Secondary interactions; 2-(imidazol-1-yl)-1-phenylethanone; Organic acids; PROTON-TRANSFER COMPOUNDS; CRYSTAL-STRUCTURE; HYDROGEN-BOND; CARBOXYLIC-ACIDS; SOLID-STATE; STRUCTURAL-CHARACTERIZATION; SUPRAMOLECULAR ADDUCTS; MOLECULAR-STRUCTURE; COCRYSTALS; NETWORKS;
D O I
10.1016/j.molstruc.2019.04.002
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
Cocrystallization of 2-(imidazol-1-yl)-1-phenylethanone with a series of organic acids gave seven crystalline salts with the compositions: 2-(imidazolium-1-yl)-1-phenylethanone trifluoroacetate (1) [(HL)(+) center dot (tfa)(-), tfa(-) = trifluoroacetate], bis(2-(imidazolium-1-yl)-1-phenylethanone) bis(hydrogen fumarate) monohydrate (2) [(HL)(2)(2+) center dot (Hfum)(2)(2-)center dot H2O, Hfum = hydrogen fumarate], 2-(imidazolium-1-yl)-1-phenylethanone 3,5-dinitrobenzoate (3) [(HL)(+) center dot (dnb(-)), dnb(-) = 3,5-dinitrobenzoate], 2-(imidazolium-1-yl)-1-phenylethanone 5-sulfosalicylate (4) [(HL)(+) center dot (Hssa(-)), Hssa(-) = 5-sulfosalicylate], bis(2-(imidazolium-1-yl)-1-phenylethanone ) 1,5- naphthalenedisulfonate (5) [(HL)(2)(2+) center dot (npa(2-)), npa(2-) = 1,5-naphthalenedisulfonate], 2-(imidazolium-1-yl)-1-phenylethanone 3-nitrohydrogenphthalate (6) [(HL+) center dot (Hnpta(-)), Hnpta(-) = 3-nitrohydrogenphthalate], and 2-(imidazolium-1-yl)-1-phenylethanone 4-nitrohydrogenphthalate (7) [(HL)(+) center dot (Hnpa)(-), Hnpa(-) = 4-nitrohydrogenphthalate]. The seven salts have been characterized by XRD technique, IR, and elemental analysis, and the melting points of all salts were also reported. Their structural and supramolecular aspects are fully analyzed. The result reveals that in all the seven investigated crystalline solids the 3-N of the ring in 2-(imidazol-1-yl)-1-phenylethanone moieties are protonated when the organic acids are deprotonated, and the crystal packing is interpreted in terms of the strong charge-assisted N-H center dot center dot center dot O H-bond from the NH+ and the deprotonated acidic groups. In addition to the N-H center dot center dot center dot O H-bond, the O-H center dot center dot center dot O H-bonds were also found at 2, 4, and 6-7. Further analysis of the crystal packing of the salts told that a different set of additional CH-O/CH2-O, CH-F, F-F, CH-pi, OH-pi, O-O, O-C-pi, and O-pi associations contribute to the stabilization and expansion of the total 3D framework structures. For the interplay of the various weak nonbonding interactions these structures adopted homo or hetero supramolecular synthons or both. The classical supramolecular synthons of R-2(2)(7) and R-2(2)(8), usually observed in organic solids of organic acids with imidazole, were again shown to be participated in constructing most of these H-bonding networks. (C) 2019 Published by Elsevier B.V.
引用
收藏
页码:81 / 93
页数:13
相关论文
共 50 条
  • [41] Synthesis, anticancer activity and docking studies of N-phenyl-2-(2-((4-phenyl piperazin-1-yl) methyl)-1H-benzo [d] imidazol-1-yl) acetamides
    Boddu, Lingaiah
    Pagudala, Ashok Kumar
    Gandamalla, Durgaiah
    Balabadra, Saikrishna
    Manga, Vijjulatha
    Yellu, Narsimha Reddy
    Subhashini, N. J. P.
    JOURNAL OF MOLECULAR STRUCTURE, 2018, 1166 : 362 - 368
  • [42] (S)-2-(1H-Imidazol-1-yl)-3-phenyl-propanol
    Yang, Zuxing
    Wei, Siping
    Wang, Wenhai
    Chen, Hua
    Lan, Jingbo
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O631 - U1479
  • [43] Synthesis, Staructure and Redox Properties of Cu(II) Chelate Complexes on the Basis of 2-(Hydroxyphenyl)-1H-benzo[d]imidazol-1-yl Phenol Ligands
    Ivakhnenko, Eugeny P.
    Knyazev, Pavel A.
    Vitkovskaya, Yulia G.
    Popov, Leonid D.
    Lyssenko, Konstantin A.
    Demidov, Oleg P.
    Starikov, Andrey G.
    Borodkin, Gennady S.
    Minkin, Vladimir I.
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2021, 2021 (21) : 2055 - 2062
  • [44] 4-(E)-2-[3-(3-[(E)-2-(4-Cyanophenyl)-1-diazenyl]perhydrobenzo[d]imidazo-1-ylmethyl)perhydrobenzo[d]imidazol-1-yl]-1-diazenylbenzonitrile:: X-ray crystal structure
    Glister, JF
    Vaughan, K
    Bertolasi, V
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2004, 34 (03) : 175 - 180
  • [45] Synthesis, Crystal Structure, and Luminescent Sensing Properties of a Supramolecular 3D Zinc(II) Metal-Organic Framework with Terephthalate and Bis(imidazol-1-yl)methane Linkers
    Matveevskaya, Vladislava V. V.
    Pavlov, Dmitry I. I.
    Ryadun, Alexey A. A.
    Fedin, Vladimir P. P.
    Potapov, Andrei S. S.
    INORGANICS, 2023, 11 (07)
  • [46] Synthesis of some novel 1-(2-naphthyl)-2-(imidazol-1-yl)ethanone oxime ester derivatives and evaluation of their anticonvulsant activity
    Karakurt, Arzu
    Alagoz, Mehmet A.
    Sayoglu, Burcu
    Calis, Unsal
    Dalkara, Sevim
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 57 : 275 - 282
  • [47] Synthesis and antifungal activities of some aryl [3-(imidazol-1-yl/triazol-1-ylmethyl) benzofuran-2-yl] ketoximes
    Gundogdu-Karaburun, Nalan
    Benkli, Kadriye
    Tunali, Yagmur
    Ucucu, Umit
    Demirayak, Seref
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (05) : 651 - 656
  • [48] 2-[2-(5-Bromothiophen-2-yl)-4,5diphenyl-1H-imidazol-1- yl]-3-phenylpropan-1-ol
    Gao, Jie
    Yang, Liangru
    Mai, Wenpeng
    Yuan, Jinwei
    Mao, Pu
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1379 - +
  • [49] Novel 2-(2-(benzylthio)-1H-benzo[d]imidazol-1-yl)acetic acids: Discovery and hit-to-lead evolution of a selective CRTh2 receptor antagonist chemotype
    Pothier, Julien
    Riederer, Markus A.
    Peter, Oliver
    Leroy, Xavier
    Valdenaire, Anja
    Gnerre, Carmela
    Fretz, Heinz
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (14) : 4660 - 4664
  • [50] 1-[2-(p-Tolyl)-1-diazenyl]-3-({3-[2-(p-tolyl)-1-diazenyl] perhydrobenzo[d]imidazol-1-yl}methyl)perhydrobenzo[d]imidazole: synthesis,characterization and X-ray crystal structure
    Julie F. Glister
    Hilary Jenkins
    Keith Vaughan
    Journal of Chemical Crystallography, 2006, 36 : 445 - 452