Oxaziridine (C-CH3NO), C-CH2NO Radicals and Cl, NH2 and Methyl Derivatives of Oxaziridine; Structures and Quantum Chemical Parameters

Taghizadeh, Mohammad Taghi; Vatanparast, Morteza; Nasirianfar, Saeed

doi:10.19261/cjm.2015.10(2).10

Cited by 4 publications

(4 citation statements)

References 52 publications

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“…3-Methyl-oxaziridine is postulated as a potential product in a kinetic study of the CH 3 C • HNH 2 + O 2 reaction, while Taghizadev et al investigated the structures of a number of methyl derivatives of oxaziridines …”

Section: Resultsmentioning

confidence: 99%

“…3-Methyl-oxaziridine is postulated as a potential product in a kinetic study of the CH 3 C • HNH 2 + O 2 reaction, 92 while Taghizadev et al investigated the structures of a number of methyl derivatives of oxaziridines. 93 This chiral system exists mainly (71.2%) as the trans form with the NH and methyl groups on opposite sides of the ring with the cis or same-side conformer at +2.25 kJ mol −1 (28.8%).…”

Section: ■ Theoretical Methodsmentioning

confidence: 99%

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C₂H₅NO Isomers: From Acetamide to 1,2-Oxazetidine and Beyond

Simmie

2022

J. Phys. Chem. A

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This work documents the properties of a number of isomers of molecular formula C 2 H 5 NO from the most stable, acetamide, through 1,2-oxazetidine and including even higher energy species largely of a dipolar nature. Only two of the isomers have been detected in emissions from the interstellar medium (ISM); possible further candidates are identified, and the likelihood of their being detectable is considered. In general, hardly any of these compounds have been discussed in the existing chemical literature, so this work represents an important contribution extending the canon of chemical bonding which can contribute to machine learning, providing a more exacting test of AI applications. The presence in the ISM of acetamide, CH 3 C(O)NH 2 , is the subject of current debate with no clear and obvious paths to its formation; it is shown that a 1,3-[H]-transfer from ( E,Z )-ethanimidic acid, CH 3 C(OH)=NH, is feasible in spite of an energy barrier of 130 kJ mol –1 . It is speculated that imidic acid can itself be formed from abundant precursors, H 2 O and CH 3 C≡N, in an acid-induced, water addition, autocatalytic reaction on water–ice grains. H 3 CC≡N H 3 CC≡NH + + H 2 O H 3 CC(O + H 2 )=NH H 3 CC(OH)=NH + H 3 O +

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Section: Resultsmentioning

confidence: 99%

Section: ■ Theoretical Methodsmentioning

confidence: 99%

C₂H₅NO Isomers: From Acetamide to 1,2-Oxazetidine and Beyond

Simmie

2022

J. Phys. Chem. A

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“…Oxaziridine molecule has been previously investigated by Taghizadeh et al [11], who applied Fukui functions [12] and studied the topography of molecular electrostatic potential, MEP, at the DFT(B3LYP)/6-311++G(d,p) level. Calculated Fukui functions show a carbon atom as possible site for electrophilic or nucleophilic attack.…”

Section: Introductionmentioning

confidence: 99%

Topological analysis of the electron localisation function (ELF) applied to the electronic structure of oxaziridine: the nature of N-O bond

2019

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Topological analysis of the electron localisation function (ELF), natural bond orbital and Wiberg bond index calculations have been applied to study the electronic structure of the oxaziridine molecule with a special focus on the nitrogen-oxygen bond. The calculations have been performed at the DFT(B3LYP, CAM-B3LYP, ωB97XD, M06-L, M06-2X) and post-Hartree-Fock (CCSD(T) and CASSCF) computational levels with applied aug-cc-pVTZ basis set. Nature of NO bonding has been characterised by two resonance forms, N + O − and N − O + , owing to a very small population (< 0.60e) of the bonding basin V(N,O), localised in the ELF field for the NO region. The importance of electron correlation effects for the description of the NO bonding has been observed in the CASSCF calculations. The orbital description (Wiberg, NBO) differs from topological characterisation, indicating a single NO bond.

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“…3 C • HNH 2 + O 2 reaction 82while Taghizadev et al investigated the structures of a number of methyl derivatives of oxaziridines 83. …”

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confidence: 99%

C2H5NO Isomers: from Acetamide to1,2-Oxazetidine and Beyond

Simmie

2021

Preprint

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This work documents the properties of a number of isomers of molecular formula C2H5NO from the most stable, acetamide, through 1,2-oxazetidine and including even higher energy species largely of a dipolar nature. Only two of the isomers have been detected in emissions from the interstellar medium (ISM); possible further candidates are identifi�ed and the likelihood of their being detectable are considered. In general hardly any of these compounds have featured in the existing chemical literature so this work represents an important contribution extending the canon of chemical bonding which can contribute to machine-learning | providing a more exacting test of AI applications. The presence of acetamide, CH3C(O)NH2, is the subject of current debate with no clear and obvious paths to its formation; it is shown that a 1,3[H]-transfer from (E,Z ) ethanimidic acid, CH3C(OH){{NH, is feasible in spite of an energy barrier of 130 kJ/mol. It is speculated that the imidic acid can itself be formed from abundant precursors, H2O and CH3C{{{N, in an acid-induced, water addition, auto-catalytic reaction on water-ice grains.

show abstract

Oxaziridine (C-CH3NO), C-CH2NO Radicals and Cl, NH2 and Methyl Derivatives of Oxaziridine; Structures and Quantum Chemical Parameters

Cited by 4 publications

References 52 publications

C₂H₅NO Isomers: From Acetamide to 1,2-Oxazetidine and Beyond

C₂H₅NO Isomers: From Acetamide to 1,2-Oxazetidine and Beyond

Topological analysis of the electron localisation function (ELF) applied to the electronic structure of oxaziridine: the nature of N-O bond

C2H5NO Isomers: from Acetamide to1,2-Oxazetidine and Beyond

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Oxaziridine (C-CH3NO), C-CH2NO Radicals and Cl, NH2 and Methyl Derivatives of Oxaziridine; Structures and Quantum Chemical Parameters

Cited by 4 publications

References 52 publications

C2H5NO Isomers: From Acetamide to 1,2-Oxazetidine and Beyond

C2H5NO Isomers: From Acetamide to 1,2-Oxazetidine and Beyond

Topological analysis of the electron localisation function (ELF) applied to the electronic structure of oxaziridine: the nature of N-O bond

C2H5NO Isomers: from Acetamide to1,2-Oxazetidine and Beyond

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C₂H₅NO Isomers: From Acetamide to 1,2-Oxazetidine and Beyond

C₂H₅NO Isomers: From Acetamide to 1,2-Oxazetidine and Beyond