Gas-phase pyrolysis of N-alkoxyphthalimides to functionally substituted aldehydes: kinetic and mechanistic study

Al-Etaibi, Alya M.; Al‐Awadi, Nouria A.; Ibrahim, Maher R.; Ibrahim, Yehia A.

doi:10.3998/ark.5550190.0011.a13

Cited by 8 publications

(6 citation statements)

References 6 publications

(4 reference statements)

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“…Gas phase pyrolysis has been used as a means of organic synthesis 18 , 27 – 33 . For example, flash vacuum pyrolysis of N-alkoxyphthalimides at 673–773 K and 0.02 Torr yielded the corresponding substituted aldehydes and phthalimide 27 .…”

Section: Introductionmentioning

confidence: 99%

Pyrolytic elimination of ethylene from ethoxyquinolines and ethoxyisoquinolines: a computational study

Abdel-Rahman

Shibl

Mahmoud

2023

Sci Rep

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This work reports a thermo-kinetic study on unimolecular thermal decomposition of some ethoxyquinolines and ethoxyisoquinolines derivatives (1-ethoxyisoquinoline (1-EisoQ), 2-ethoxyquinoline (2-EQ), 3-ethoxyquinoline (3-EQ), 3-ethoxyisoquinoline (3-EisoQ), 4-ethoxyquinoline (4-EQ), 4-ethoxyisoquinoline (4-EisoQ), 5-ethoxyquinoline (5-EQ), 5-ethoxyisoquinoline (5-EisoQ), 8-ethoxyquinoline (8-EQ) and 8-ethoxyisoquinoline (8-EisoQ)) using density functional theory DFT (BMK, MPW1B95, M06-2X) and ab initio complete basis set-quadratic Becke3 (CBS-QB3) calculations. In the course of the decomposition of the investigated systems, ethylene is eliminated with the production of either keto or enol tautomer. The six-membered transition state structure encountered in the path of keto formation is much lower in energy than the four-membered transition state required to give enol form. Rate constants and activation energies for the decomposition of 1-EisoQ, 2-EQ, 3-EQ, 3-EisoQ, 4-EQ, 4-EisoQ, 5-EQ, 5-EisoQ, 8-EQ, and 8-EisoQ have been estimated at different temperatures and pressures using conventional transition state theory combined with Eckart tunneling and the unimolecular statistical Rice–Ramsperger–Kassel–Marcus theories. The tunneling correction is significant at temperatures up to 1000 K. Rate constants results reveal that ethylene elimination and keto production are favored kinetically and thermodynamically over the whole temperature range of 400–1200 K and the rates of the processes under study increase with the rising of pressure up to 1 atm.

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Section: Introductionmentioning

confidence: 99%

Pyrolytic elimination of ethylene from ethoxyquinolines and ethoxyisoquinolines: a computational study

Abdel-Rahman

Shibl

Mahmoud

2023

Sci Rep

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Section: Introductionmentioning

confidence: 99%

“…Gas phase pyrolysis has been used as a means of organic synthesis [28][29][30][31][32][33][34][35]. For example, flash vacuum pyrolysis of N-alkoxyphthalimides at 673-773 K and 0.02 Torr yielded the corresponding substituted aldehydes and phthalimide [28]. Gas-phase pyrolysis of N-(1Hbenzimidazol-2-yl)-N'-arylidenehydrazines produced arylnitriles, 2-aminobenzimid-azole, 2,4,5-triphenylimidazole, 1,3-diphenyl-8H-2,3a,8-triazacyclopenta [a]indene, and 5,11diphenyl-6H,12H-dibenzimidazo[1,2-a];1',2'-d]pyrazine [29].…”

Section: Introductionmentioning

confidence: 99%

Mahmoud, A. M.1; E. A. Ali1; Manal A. M. Hassan2* and Asmaa S. A. Sayed1 1 Department of Agronomy, Faculty of Agriculture, Assiut University, Assiut, 71526, Egypt 2 Food Science and Technology Department, Faculty of Agriculture, Assiut University, Assiut 71526, Egypt

Mahmoud

Ali

Hassan

et al. 2019

Journal of Food and Dairy Sciences

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designed BPF are as follows: W 1 5 1.5 mm, W 2 5 1.0 mm, W 3 5 0.6 mm, W 4 5 1.0 mm, W 5 5 0.88 mm, L 1 5 5.7 mm, L 2 5 5.88 mm, L 3 5 9.23 mm, L 4 5 11.0 mm, L 5 5 12.0 mm, L 6 5 3.51 mm, d 1 5 0.17 mm, d 2 5 0.17 mm, d 3 5 0.17 mm, and d 4 5 0.17 mm.ABSTRACT: In this article, an ultrawideband (UWB) antenna with triple band-rejection characteristics is proposed. The antenna is compact with size of 22.5 3 24 mm 2 . Matching between a sector-disk shaped radiating patch and the 50-X microstrip line is manipulated through a proximity-feed technique. An elliptically-shaped aperture is etched in the ground plane to enhance the antenna bandwidth. Double shunt stubs are used to get more enhancement of the impedance bandwidth of the

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“…Relevant to this work is the previous study of the FC(O)CN molecule , and the corresponding aldehyde, HC(O)CN. The latter has previously been generated by several pyrolytic methods and studied by microwave, infrared, and electronic spectroscopies. − …”

Section: Introductionmentioning

confidence: 99%

Generation, Spectroscopy, and Structure of Cyanoformyl Chloride and Cyanoformyl Bromide, XC(O)CN

et al. 2012

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Cyanoformyl chloride and cyanoformyl bromide, XC(O)CN (X = Cl and Br), have been investigated in the gas phase by UV photoelectron and mid-infrared spectroscopies. The ground-state geometries of the neutral molecules have been obtained from quantum-chemical calculations at the B3LYP and CCSD(T) levels using the aug-cc-pVTZ basis set. The individual spectroscopies provide a detailed investigation into the vibrational and electronic character of the molecules and are supported by quantum-chemical calculations. The results are compared to data for structurally and chemically related molecules.

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Gas-phase pyrolysis of N-alkoxyphthalimides to functionally substituted aldehydes: kinetic and mechanistic study

Abstract: Flash vacuum Pyrolysis (FVP) of primary N-alkoxyphthalimides at 400-500 o C and 0.02 Torr gave functionally substituted aldehydes. A mechanism of this pyrolytic transformation was proposed based on the kinetic data and product analysis.

Cited by 8 publications

References 6 publications

Pyrolytic elimination of ethylene from ethoxyquinolines and ethoxyisoquinolines: a computational study

Pyrolytic elimination of ethylene from ethoxyquinolines and ethoxyisoquinolines: a computational study

Mahmoud, A. M.1; E. A. Ali1; Manal A. M. Hassan2* and Asmaa S. A. Sayed1 1 Department of Agronomy, Faculty of Agriculture, Assiut University, Assiut, 71526, Egypt 2 Food Science and Technology Department, Faculty of Agriculture, Assiut University, Assiut 71526, Egypt

Generation, Spectroscopy, and Structure of Cyanoformyl Chloride and Cyanoformyl Bromide, XC(O)CN

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