The mechanisms of nucleophilic substitution in 1-methyl-3,4,5-trinitropyrazole

The mechanisms of nucleophilic substitution in 1-methyl-3,4,5-trinitropyrazole Full article

Journal

Computational and Theoretical Chemistry
ISSN: 2210-2728 , E-ISSN: 2210-271X

Output data

Year: 2014, Volume: 1033, Pages: 31-42 Pages count : 12 DOI: 10.1016/j.comptc.2014.01.018

Authors

Kletskii Mikhail Е. ¹ , Burov Оleg N. ² , Dalinger Igor L. ³ , Shevelev Svyatoslav А. ³

Affiliations

1	Department of Chemistry, Southern Federal University, 7, Zorge St., 344090 Rostov-on-Don, Russian Federation
2	Southern Scientific Center, Russian Academy of Sciences, 41, Chehova St., 344006 Rostov-on-Don, Russian Federation
3	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninskiy Prospect, 119991 Moscow, Russian Federation

The nitro group nucleophilic substitution reactions in 1-methyl-3,4,5-trinitropyrazole (MTNP) were studied quantum chemically by DFT and MP2 methods in the gas phase and methanol (6-31G∗∗ basis set, PCM approach). Also the calculations of Parr’s reactivity indices were used. It was shown that these processes occur as synchronous bi- or trimolecular attacks by ammonia molecule or ammonia dimer. Regardless of process type, effects of solvent are the key factors defining its direction. That distinguishes principally the nucleophilic substitution reactions in MTNP from similar processes with 3,4,5-trinitropyrazole (TNP) participation which occurs through substrate deprotonation.

Kletskii M.Е. , Burov О.N. , Dalinger I.L. , Shevelev S.А.
The mechanisms of nucleophilic substitution in 1-methyl-3,4,5-trinitropyrazole
Computational and Theoretical Chemistry. 2014. V.1033. P.31-42. DOI: 10.1016/j.comptc.2014.01.018 Scopus OpenAlex

≡ Scopus:	2-s2.0-84894505271
≡ OpenAlex:	W2041916182