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A theoretical approach to the regioselectivity in 1,3‐dipolar cycloadditions of diazoalkanes, hydrazoic acid and nitrous oxide to acetylenes, phosphaalkynes and cyanides
Author(s) -
Nguyen Loc Thanh,
Proft Frank De,
Dao Van Luong,
Nguyen Minh Tho,
Geerlings Paul
Publication year - 2003
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.653
Subject(s) - chemistry , hydrazoic acid , regioselectivity , cycloaddition , computational chemistry , reactivity (psychology) , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
The 1,3‐dipolar cycloadditions of diazoalkanes (R 2 CNN), hydrazoic acid (HNNN) and nitrous oxide (N 2 O) to some simple dipolarophiles such as acetylenes, phosphaalkynes and cyanides were studied using quantum chemical calculations at the B3LYP/6–311++G(d,p) level and, in the simplest case, using also the CCSD(T) method. Along with frontier molecular orbital coefficients, the local softness being a DFT‐based reactivity criterion is established as a useful tool to predict the regioselectivity in these cycloaddition reactions. Copyright © 2003 John Wiley & Sons, Ltd.