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A quantum‐chemical study on the Mannich reaction with polynitromethanes
Author(s) -
Xiao HeMing,
Tang ZeHua
Publication year - 1989
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19890070402
Subject(s) - chemistry , nucleophile , mannich reaction , measure (data warehouse) , electrophile , computational chemistry , quantum chemical , mannich base , cationic polymerization , weighting , amine gas treating , computation , quantum , mindo , organic chemistry , molecule , quantum mechanics , mathematics , catalysis , algorithm , medicine , physics , database , computer science , radiology
According to the results of SCF‐CNDO/2 computation, we propose employing the “ladder weighting summation” to define a G e index which is used to measure the relative magnitude of the nucleophilicity of the relevant amine and pseudo acid components in a Mannich reaction. We also put forward an A e index to measure the relative magnitude of the electrophilicity of methyleneamine cationic species in the same reaction. A combined use of both G e and A e indices is suggested to evaluate the feasibility of a Mannich reaction for the polynitromethanes and the stability of the products. These results are consistent with those conclusions drawn from “soft‐hard acid‐base theory”.