Synthesis, Crystallographic and Spectral Studies of 3-(4-(Phenylamino) Phenylamino)Cyclohex-2-Enone

被引:0
|
作者
Timur, Mahir [1 ]
Kavak, Guelten [2 ]
Senoz, Hulya [1 ]
Ide, Semra [3 ]
Tunoglu, Nazan [1 ]
机构
[1] Hacettepe Univ, Fac Sci, Dept Chem, TR-06800 Beytepe, Turkey
[2] Dicle Univ, Dept Phys, Fac Sci & Art, TR-21280 Diyarbakir, Turkey
[3] Hacettepe Univ, Fac Engn, Dept Engn Phys, TR-06800 Beytepe, Turkey
关键词
Schiff base; beta-Enaminone; Cyclohexanedione; Crystal structure; Spectroscopic studies; Tautomerism; O-17; NMR-SPECTRA; ENAMINONES; HYDROLYSIS; COMPLEXES; MECHANISM; EFFICIENT; CATALYST;
D O I
10.1007/s10870-009-9664-3
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
The title compound, 3-(4-(phenylamino)phenylamino)cyclohex-2-enone, beta- enaminone of 1,3-cyclohexanedione and p-amino diphenylamine (C18H18N2O) was prepared and characterized by H-1-NMR, C-13-NMR, Elemental analysis and IR spectroscopy as well as single crystal X-ray diffraction. These results indicate the predominance of the keto-enol tautomerism. Molecular conformation around the central disubstituted benzene ring is affected by the tautomerism and two steric effects between side molecular groups and mono substituted benzene ring. Electron delocalizations due to these effects have been observed in the molecular structure, the structure being stabilized by some intermolecular hydrogen bonds.
引用
收藏
页码:376 / 380
页数:5
相关论文
共 50 条
  • [21] Crystal structure of 3-hydroxy-2-(4-(methylsulfonyl)-2-nitrobenzoyl)cyclohex-2-enone, C14H13NO7S
    Hou, Yan-Jun
    Chu, Wen-Yi
    Sui, Jun
    Sun, Zhi-Zhong
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2010, 225 (03): : 465 - 466
  • [22] Theoretical investigation on rearrangement mechanism of 2-(2-methyiallyl)-3-(3-methylbnta-1, 2-dienyl) cyclohex-2-enone
    Zhu Yuan-Qiang
    Guo Yong
    Xie Dai-Qian
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2008, 29 (02): : 385 - 388
  • [23] 4-Dichloromethy1-4-methy1-5-(nitro-methyl)cyclohex-2-enone
    Novakovic, Sladjana B.
    Rodic, Marko V.
    Jacimovic, Zeljko K.
    Ratkovic, Zoran
    Sukdolak, Slobodan
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1638 - +
  • [24] (R)-2-Methyl-5-[(R)-2,4,4,4-tetrachlorobutan-2-yl] cyclohex-2-enone
    Boualy, Brahim
    Harrad, Mohamed Anouar
    El Firdoussi, Larbi
    Ali, Mustapha Ait
    Stoeckli-Evans, Helen
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : 02451 - +
  • [25] Synthesis, anti-microbial activity and docking studies of 3-(2-(phenylamino)thiazol-4-yl)-2H-chromen-2-ones and ethyl 2-(2-(phenylamino)thiazol-4-yl)acetates
    Devulapally, Srikrishna
    Alvala, Mallika
    Dubey, Pramod Kumar
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2017, 56 (01): : 96 - 105
  • [26] Synthesis and Biological Properties of 3-(2-Hydroxyethyl)-2-(phenylamino)quinazolin-4(3H)-ones
    Yang, Xuhong
    Wang, Xiang
    Wu, Minghu
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (05) : 1015 - 1020
  • [27] Straightforward Synthesis of Nonconjugated Cyclohex-3-enone and Conjugated 4-Methylenecyclohex-2-enone Derivatives
    Kuttner, Julian R.
    Warratz, Svenja
    Hilt, Gerhard
    SYNTHESIS-STUTTGART, 2012, 44 (09): : 1293 - 1303
  • [28] The Beckmann rearrangement of cyclohex-2-enone oximes. Synthesis of 4,5-diphenyl-2,3,4,5-tetrahydro-1H-azepin-2-one
    Lyga, JW
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (06) : 1631 - 1635
  • [29] Design, Synthesis, and Herbicidal Activity of Substituted 3-(Pyridin-2-yl)Phenylamino Derivatives
    Chen, Zhongyin
    Cai, Hui
    Zhang, Xiao
    Zhang, Meng
    Hao, Ge-Fei
    Jin, Zhichao
    Ren, Shichao
    Chi, Yonggui Robin
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2024, 72 (05) : 2501 - 2511
  • [30] Synthesis of dimedone-annelated heterocycles:: Regioselective heterocyclization of 2-(Cyclohex-2′-enyl)-5,5-dimethyl-3-hydroxy cyclohex-2-enone
    Majumdar, KC
    Samanta, SK
    Basu, PK
    SYNTHETIC COMMUNICATIONS, 2003, 33 (04) : 679 - 686