Methylene Group Transfer in Carbonyl Compounds Discovered in silico and Detected Experimentally | Zendy

Gridnev Ilya D. | Zendy; Zherebker Alexander | Zendy; Kostyukevich Yury | Zendy; Nikolaev Eugene | Zendy

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Methylene Group Transfer in Carbonyl Compounds Discovered in silico and Detected Experimentally

Author(s) -

Gridnev Ilya D.,

Zherebker Alexander,

Kostyukevich Yury,

Nikolaev Eugene

Publication year - 2019

Publication title -

chemphyschem

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.016

H-Index - 140

eISSN - 1439-7641

pISSN - 1439-4235

DOI - 10.1002/cphc.201800945

Subject(s) - benzonitrile , chemistry , methylene , acetone , mass spectrometry , electrospray ionization , carbonyl group , medicinal chemistry , photochemistry , computational chemistry , organic chemistry , chromatography

A previously unknown transformation of aldehydes, ketones, and carboxylic acid derivatives leads to the formation of substituted oxiranes, aziridines, and azirines as shown by DFT and MP2 computations. Formations of 2,2‐dimethyloxirane‐d 8 from acetone‐d 6 , phenylazirine‐d 2 from benzonitrile and 2‐methyl‐2‐(4‐hydroxyphenyl)‐oxirane from 4‐hydroxyacetophenone were detected experimentally by electrospray ionization mass‐spectrometry with a heated desolvating capillary. This reaction is a truly concerted process characterized by high activation barriers (activation enthalpies 320–480 kJ mol −1 ).

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