N-allyl and N-propargyl trifluoromethanesulfonimides. Theoretical analysis


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Аннотация

Tautomers of N-allyl- and N-propargyl-substituted trifluoromethanesulfonimides (CF3SO2)2NR (R = CH2CH=CH2, Z/E-CH=CHMe, CH2C≡CH, CH=CH=CH2, C≡CCH2) were calculated by the DFT (B3LYP, wB97XD, PBE1PBE), MP2, and CBS-QB3 methods. The results were compared with the theoretical data for the corresponding amines and amides NHRR1 (R1 = H, CF3SO2). It was shown that there is no conjugation between the nitrogen atom and C=C bond and that conjugation exists with the C≡C bond with electron density displacement toward the nitrogen atom. The calculations of anions derived from N-allyl- and N-propargyl-trifluoromethanesulfonimides revealed the possibility of their rearrangement with elimination of trifluoromethanesulfinate anion and formation of its H-complex with N-(prop-2-en-1-ylidene)trifluoromethanesulfonamide or N-(prop-2-yn-1-ylidene)trifluoromethanesulfonamide.

Авторлар туралы

A. Kuzmin

Favorskii Irkutsk Institute of Chemistry, Siberian Branch; Limnological Institute, Siberian Branch

Email: bagrat@irioch.irk.ru
Ресей, ul. Favorskogo 1, Irkutsk, 664033; Ulan-Batorskaya ul. 3, Irkutsk, 664033

B. Shainyan

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Хат алмасуға жауапты Автор.
Email: bagrat@irioch.irk.ru
Ресей, ul. Favorskogo 1, Irkutsk, 664033

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