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• W2332842758 endingPage "13974" @default.
• W2332842758 startingPage "13965" @default.
• W2332842758 abstract "The anionic SN2 reactions at neutral nitrogen, Nu– + NR2Cl → NR2Nu + Cl– (R = H, Me; Nu = F, Cl, Br, OH, SH, SeH, NH2, PH2, AsH2) have been systematically studied computationally at the modified G2(+) level. Two reaction mechanisms, inversion and retention of configuration, have been investigated. The main purposes of this work are to explore the reactivity trend of anions toward NR2Cl (R = H, Me), the steric effect on the potential energy surfaces, and the leaving ability of the anion in SN2@N reactions. Our calculations indicate that the complexation energies are determined by the gas basicity (GB) of the nucleophile and the electronegativity (EN) of the attacking atom, and the overall reaction barrier in the inversion pathway is basically controlled by the GB value of the nucleophile. The retention pathway in the reactions of NR2Cl with Nu– (Nu = F, Cl, Br, OH, SH, SeH) is energetically unfavorable due to the barriers being larger than those in the inversion pathway by more than 120 kJ mol–1. Activation strain model analyses show that a higher deformation energy and a weaker interaction between deformed reactants lead to higher overall barriers in the reactions of NMe2Cl than those in the reactions of NH2Cl. Our studies on the reverse process of the title reactions suggest that the leaving ability of the anion in the gas phase anionic SN2@N reactions is mainly determined by the strength of the N–LG bond, which is related to the negative hyperconjugation inherent in NR2Nu (R = H, Me; Nu = HO, HS, HSe, NH2, PH2, AsH2)." @default.
• W2332842758 created "2016-06-24" @default.
• W2332842758 creator A5017871867 @default.
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• W2332842758 date "2011-11-03" @default.
• W2332842758 modified "2023-10-16" @default.
• W2332842758 title "Comprehensive Theoretical Studies on the Gas Phase S_N2 Reactions of Anionic Nucleophiles toward Chloroamine and <i>N</i>-Chlorodimethylamine with Inversion and Retention Mechanisms" @default.
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• W2332842758 doi "https://doi.org/10.1021/jp208887h" @default.
• W2332842758 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/21988223" @default.
• W2332842758 hasPublicationYear "2011" @default.
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