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
  • [21] THEORETICAL-STUDY OF THE THERMAL UNIMOLECULAR REARRANGEMENT OF FLUOROETHYLIDENES
    KAKKAR, R
    WALIA, V
    INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 1992, 44 (03) : 363 - 377
  • [22] Theoretical study of the thermal rearrangement of chloromethylsilanes, and its mechanism
    Bei, Yiling
    Liu, Qingyang
    Feng, Shengyu
    RESEARCH ON CHEMICAL INTERMEDIATES, 2012, 38 (09) : 2491 - 2500
  • [23] A theoretical study of regio and stereoselectivity nitration of thymol and carvacrol using DFT approach
    El Hamidi, Sana
    Khnifira, Malika
    Elhalil, Alaaeddine
    Hammal, Redouan
    Barka, Noureddine
    Sadiq, Mhamed
    Benharref, Ahmed
    Lafridi, Hind
    Zgou, Hsaine
    Abdennouri, Mohamed
    MOROCCAN JOURNAL OF CHEMISTRY, 2019, 7 (02): : 363 - 372
  • [24] DFT THEORETICAL STUDY OF SOME THIOSEMICARBAZIDE DERIVATIVES WITH COPPER
    Attar, Tarik
    Messaoudi, Boulanouar
    Benhadria, Naceur
    CHEMISTRY & CHEMICAL TECHNOLOGY, 2020, 14 (01): : 20 - 25
  • [25] A combined experimental and theoretical study of the thermal cycloaddition of aryl azides with activated alkenes
    Zeghada, Sarah
    Bentabed-Ababsa, Ghenia
    Derdour, Aicha
    Abdelmounim, Safer
    Domingo, Luis R.
    Saez, Jose A.
    Roisnel, Thierry
    Nassar, Ekhlass
    Mongin, Florence
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (11) : 4295 - 4305
  • [26] Theoretical study of the mechanism of the Wolff rearrangement of some diazocarbonyl compounds
    Arora, Ritu
    Kakkar, Rita
    COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2016, 1094 : 32 - 41
  • [27] Study on the rearrangement reaction of HClN=B: Using DFT method
    Zhu, SC
    Li, WZ
    Han, SB
    Liu, FL
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2002, 21 (02) : 201 - 205
  • [28] Theoretical Approach Using DFT Calculations of Novel Oxime Derivatives
    Shahab, Siyamak
    Sheikhi, Masoome
    Shekoohi, Khadijeh
    Kaviani, Sadegh
    Shiroudi, Abolfazl
    Zarenezhad, Elham
    BIOINTERFACE RESEARCH IN APPLIED CHEMISTRY, 2023, 13 (02):
  • [29] A comparative theoretical study of the electronic structure of some nickel(II) azides, thiocyanates, and isothiocyanates
    Abu-Eittah, RH
    El-Esawy, M
    Ghoneim, N
    Aly, AT
    CANADIAN JOURNAL OF CHEMISTRY, 1998, 76 (07) : 1006 - 1014
  • [30] Theoretical study of the physisorption of CO on metal oxide surfaces using the KSCED-DFT approach
    Vulliermet, N
    Wesolowski, TA
    Weber, J
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1998, 63 (09) : 1447 - 1459
12345