Zeng Yi, Ren Yi. Theoretical Study of Intramolecular Nucleophilic Substitution on Nitrogen[J]. Chinese Journal of Chemical Physics , 2005, 18(6): 918-924. doi: 10.1088/1674-0068/18/6/918-924
Citation: Zeng Yi, Ren Yi. Theoretical Study of Intramolecular Nucleophilic Substitution on Nitrogen[J]. Chinese Journal of Chemical Physics , 2005, 18(6): 918-924. doi: 10.1088/1674-0068/18/6/918-924

Theoretical Study of Intramolecular Nucleophilic Substitution on Nitrogen

doi: 10.1088/1674-0068/18/6/918-924
Funds:  Project supported by the Scientific Research Foudation for the Returned Chinese Scholars of State Education Ministry and Sichuan University.
  • Received Date: 2004-12-10
  • Using the -CHR-(CH2)3-NFCH3(R=H, CH3, CH2CF3, CHO, COCH3) as the computational model, the two possible intramolecular reactions, nucleophilic substitution on nitrogen and elimination reaction, were studied at the theoretical level of MP2(full)/6-31+G(d,p). The results indicate that the elimination mechanism, when the -CHR radical is more basic (R=H, CH3, CH2CF3) leading to linear products R-CH2-(CH2)3N=CH2 is preferred. In contrast, electro-withdrawing groups CHO and COCH3 on the attacking site will favor the intramolecular nucleophilic substitution of nitrogen and form 5-membered heterocyclic compounds. These theoretical predictions agree with the available experiments.
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Theoretical Study of Intramolecular Nucleophilic Substitution on Nitrogen

doi: 10.1088/1674-0068/18/6/918-924
Funds:  Project supported by the Scientific Research Foudation for the Returned Chinese Scholars of State Education Ministry and Sichuan University.

Abstract: Using the -CHR-(CH2)3-NFCH3(R=H, CH3, CH2CF3, CHO, COCH3) as the computational model, the two possible intramolecular reactions, nucleophilic substitution on nitrogen and elimination reaction, were studied at the theoretical level of MP2(full)/6-31+G(d,p). The results indicate that the elimination mechanism, when the -CHR radical is more basic (R=H, CH3, CH2CF3) leading to linear products R-CH2-(CH2)3N=CH2 is preferred. In contrast, electro-withdrawing groups CHO and COCH3 on the attacking site will favor the intramolecular nucleophilic substitution of nitrogen and form 5-membered heterocyclic compounds. These theoretical predictions agree with the available experiments.

Zeng Yi, Ren Yi. Theoretical Study of Intramolecular Nucleophilic Substitution on Nitrogen[J]. Chinese Journal of Chemical Physics , 2005, 18(6): 918-924. doi: 10.1088/1674-0068/18/6/918-924
Citation: Zeng Yi, Ren Yi. Theoretical Study of Intramolecular Nucleophilic Substitution on Nitrogen[J]. Chinese Journal of Chemical Physics , 2005, 18(6): 918-924. doi: 10.1088/1674-0068/18/6/918-924

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