Synthesis, characterization and dynamic NMR studies of a novel chalcone based N-substituted morpholine derivative

被引:11
|
作者
Baskar, R. [1 ]
Baby, C. [2 ]
Moni, M. S. [2 ]
Subramanian, K. [1 ]
机构
[1] Anna Univ, Dept Chem, Madras 600025, Tamil Nadu, India
[2] Indian Inst Technol, Sophisticated Analyt Instrument Facil, Madras 600036, Tamil Nadu, India
关键词
Morpholine; Dynamic NMR; Ring inversion; INVERSION; MOLECULES; POTENT; RING;
D O I
10.1016/j.molstruc.2013.02.029
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
The synthesis of a novel chalcone based N-substituted morpholine derivative namely, (E)-1-(biphenyl-4-yl)-3-(4-(5-morpholinopentyloxy) phenyl) prop-2-en-1-one (BMPP), using a two step protocol is reported. The compound is characterized by FTIR, GC-MS and FTNMR spectroscopy techniques. Advanced 2D NMR techniques such as gradient enhanced COSY, HSQC, HMBC and NOESY were employed to establish through-bond and through-space correlations. Dynamic NMR measurements were carried out to obtain the energy barrier to ring inversion of the morpholine moiety. (C) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码:90 / 97
页数:8
相关论文
共 50 条
  • [1] Synthesis of N-substituted morpholine nucleoside derivatives
    Nekrasov, Mikhail D.
    Lukyanenko, Evgeny R.
    Kurkin, Alexander V.
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2020, 39 (09): : 1223 - 1244
  • [2] Synthesis, dynamic NMR characterization and XRD studies of novel N,N'-substituted piperazines for bioorthogonal labeling
    Mamat, Constantin
    Pretze, Marc
    Gott, Matthew
    Koeckerling, Martin
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 2478 - 2489
  • [3] A NOVEL N-SUBSTITUTED POLYANILINE DERIVATIVE
    ARMES, SP
    DEARMITT, C
    URIBE, FA
    GOTTESFELD, S
    MOMBOURQUETTE, C
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 204 : 115 - COLL
  • [4] A NOVEL N-SUBSTITUTED POLYANILINE DERIVATIVE
    DEARMITT, C
    ARMES, SP
    WINTER, J
    URIBE, FA
    GOTTESFELD, S
    MOMBOURQUETTE, C
    POLYMER, 1993, 34 (01) : 158 - 162
  • [5] Synthesis and Characterization of N-Substituted Polybenzimidazoles
    Xu, Yewei
    Tang, Jie
    Chang, Guanjun
    Luo, Xuan
    Zhu, Fanghua
    Zhang, Lin
    ASIAN JOURNAL OF CHEMISTRY, 2013, 25 (07) : 4013 - 4016
  • [6] SYNTHESIS, CHARACTERIZATION, ANTIBACTERIAL, DNA BINDING AND MOLECULAR DOCKING STUDIES OF NOVEL N-SUBSTITUTED PHTHALIMIDES
    Nayab, Pattan Sirajuddin
    Arif, Rizwan
    Arshad, Mohd
    Rahisuddin
    HETEROCYCLIC LETTERS, 2015, 5 (02): : 223 - 239
  • [7] Synthesis and electrochemical properties of N-substituted bicarbazyl derivative
    Kim, YE
    Kwon, YS
    Lee, KS
    Park, JW
    Seo, HJ
    Kim, TW
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2004, 424 : 153 - +
  • [8] Synthesis, Characterization, Thermal and Antimicrobial studies of N-substituted Sulfanilamide derivatives
    Lahtinen, Manu
    Kudva, Jyothi
    Hegde, Poornima
    Bhat, Krishna
    Kolehmainen, Erkki
    Nonappa
    Venkatesh
    Naral, Damodara
    JOURNAL OF MOLECULAR STRUCTURE, 2014, 1060 : 280 - 290
  • [9] Synthesis and Characterization of Novel Ionic Liquids: N-Substituted Aziridinium Salts
    Duriska, Martin B.
    Grondin, Joseph
    Servant, Laurent
    Birot, Marc
    Deleuze, Herve
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (03) : 652 - 657
  • [10] Synthesis, Antiviral and Cytotoxicity Studies of Novel N-substituted Indophenazine Derivatives
    Selvam, P.
    Lakra, D. R.
    Pannecouque, C.
    de Clercq, E.
    INDIAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2012, 74 (03) : 275 - U97