Jump to main content
Jump to site search

Issue 6, 2015
Previous Article Next Article

Regioselective nucleophilic aromatic substitution reactions of 5,7-dinitroquinazoline-4-one and 5,7-dinitroquinazoline-4-thione with methylamine: a mechanistic consideration

Author affiliations

Abstract

The microcosmic mechanism of nucleophilic aromatic substitution of the nitro groups of 5,7-dinitroquinazoline-4-one with methylamine has been investigated in gas phase as well as in solvent media within the formalism of density functional theory. The free energy profiles along the reaction route, structural parameters, charge analysis and frontier molecular orbitals provide sufficient evidence to conclude that no stable intermediates are formed during the reaction course and a concerted mechanism is followed in this nucleophilic substitution. The regioselectivity involved in the reaction is attributed to intramolecular hydrogen bonding (N–H–O[double bond, length as m-dash]C) that stabilises the peri-transition state. Similar to carbonyls, thiocarbonyls have also shown the regioselective attack of amines at the peri-position of 5,7-dinitroquinazoline-4-thione through intramolecular hydrogen bonding (N–H–S[double bond, length as m-dash]C).

Graphical abstract: Regioselective nucleophilic aromatic substitution reactions of 5,7-dinitroquinazoline-4-one and 5,7-dinitroquinazoline-4-thione with methylamine: a mechanistic consideration

Back to tab navigation

Supplementary files

Publication details

The article was received on 02 Feb 2015, accepted on 10 Mar 2015 and first published on 10 Mar 2015


Article type: Paper
DOI: 10.1039/C5NJ00291E
New J. Chem., 2015,39, 4351-4358

  •   Request permissions

    Regioselective nucleophilic aromatic substitution reactions of 5,7-dinitroquinazoline-4-one and 5,7-dinitroquinazoline-4-thione with methylamine: a mechanistic consideration

    A. Singh and N. Goel, New J. Chem., 2015, 39, 4351
    DOI: 10.1039/C5NJ00291E

Search articles by author

Spotlight

Advertisements