A theoretical study of the thermal Curtius rearrangement of some cinnamoyl azides using the DFT approach

被引：1
|
作者：
Abu-Eittah, Rafie H. [1 ]
Hassan, Walid M. I. [1 ]
Zordok, W. [2 ]
机构：
[1] Cairo Univ, Dept Chem, Fac Sci, Giza, Egypt
[2] Zagazig Univ, Dept Chem, Fac Sci, Zagazig, Egypt
来源：
JOURNAL OF STRUCTURAL CHEMISTRY | 2015年 / 56卷 / 04期
关键词：
Curtius rearrangement; cinnamoyl azides; DFT treatment; one stage mechanism; ACYL AZIDES; DENSITY; SPECTRA;
D O I：
10.1134/S0022476615040046
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The thermal Curtius rearrangement of cinnamoyl azide, 1-azido-3-phenylprop-2-ene-1-one, and the reactions of some of its derivatives is studied theoretically using the DFT-B3LYP/6-31G(d,p) approach. The potential energy surface profiles of the rearrangement are calculated. The transition state was located and confirmed. The Curtius rearrangement of the studied compounds is a one-stage, discrete reaction. A weak effect of substitution on the reaction rate is due to the unique, localized pi system of the studied molecules; strong opposing dipoles span the whole molecule.
引用
收藏
页码：628 / 641
页数：14
相关论文
共 50 条
  • [31] Theoretical study of the pyridyl-cholestane formation pathway using DFT: A stepwise mechanistic approach
    Sharma, Kamlesh
    Priyanka
    STEROIDS, 2025, 216
  • [32] Theoretical approach to the corrosion inhibition efficiency of some quinoxaline derivatives of steel in acid media using the DFT method
    Zarrouk, A.
    El Ouali, I.
    Bouachrine, M.
    Hammouti, B.
    Ramli, Y.
    Essassi, E. M.
    Warad, I.
    Aouniti, A.
    Salghi, R.
    RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (03) : 1125 - 1133
  • [33] Theoretical approach to the corrosion inhibition efficiency of some quinoxaline derivatives of steel in acid media using the DFT method
    A. Zarrouk
    I. El Ouali
    M. Bouachrine
    B. Hammouti
    Y. Ramli
    E. M. Essassi
    I. Warad
    A. Aouniti
    R. Salghi
    Research on Chemical Intermediates, 2013, 39 : 1125 - 1133
  • [34] Negative ion Wolff rearrangement of some diazoketones: A theoretical mechanistic study
    Arora, Ritu
    Kakkar, Rita
    COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2017, 1106 : 50 - 57
  • [35] The aza-Payne rearrangement: A theoretical DFT study of the counter-ion and solvent effects
    Bouyacoub, A
    Volatron, F
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (24) : 4143 - 4150
  • [36] Theoretical Approach of the Adsorption of Herbicide Amitrole on the Soil using DFT Method
    Tazi, Rabia
    El Hadki, Hamza
    Salah, Mohammed
    Zrineh, Abdallah
    El Azzouzi, Mohammed
    Komiha, Najia
    ORIENTAL JOURNAL OF CHEMISTRY, 2018, 34 (03) : 1240 - 1248
  • [37] MECHANISTIC STUDY OF THERMAL REARRANGEMENT OF TETRAARYLHYDRAZINES - THERMOLYSIS OF SOME DEUTERATED TETRAARYLHYDRAZINES
    WELZEL, P
    DIETZ, C
    ECKHARDT, G
    CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (11): : 3550 - 3565
  • [38] A Theoretical Study of Structure and Corrosion Inhibition of Some Heterocyclic Imidazoles: DFT Investigation
    Mamad, Dyari Mustafa
    Omer, Peshang Khdir
    Rasul, Hazhar Hamad
    Qadr, Hiwa Mohammad
    SURFACE ENGINEERING AND APPLIED ELECTROCHEMISTRY, 2023, 59 (04) : 489 - 501
  • [39] From germolane to germylenes: a theoretical DFT study of thermal decomposition pathways and reactivity
    Badran, Ismail
    JOURNAL OF COORDINATION CHEMISTRY, 2024, 77 (20-21) : 2440 - 2452
  • [40] Theoretical study of the corrosion inhibition of some bipyrazolic derivatives: a conceptual DFT investigation
    N. Boussalah
    S. Ghalem
    S. El Kadiri
    B. Hammouti
    R. Touzani
    Research on Chemical Intermediates, 2012, 38 : 2009 - 2023
12345