Premium
A Theoretical Discussion of Further Substitution in Disubstituted Naphthalenes. Part III‐The Further Nitration of the Dinitro‐naphthalenes
Author(s) -
Hodgson H. H.,
Ward E. R.
Publication year - 1947
Publication title -
journal of the society of dyers and colourists
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.297
H-Index - 49
eISSN - 1478-4408
pISSN - 0037-9859
DOI - 10.1111/j.1478-4408.1947.tb02462.x
Subject(s) - nitration , substitution (logic) , chemistry , naphthalene , computational chemistry , electrophilic aromatic substitution , medicinal chemistry , organic chemistry , philosophy , linguistics
The mono‐ and di‐nitrations of the 1:3‐, 1:4‐, 1:5‐, 1:6‐, 1:8‐, 2:6‐ and 2:7‐dinitronaphthalones are discussed from the standpoint of the Veselý and Jake quinonoid hypothesis of naphthalene substitution as modified by modern electronic and resonance theory 7 . Further, the readier nitration of β‐ compared with α‐nitronaphthalenes, the facile dinitration of 2:6‐ and 2:7‐dinitronaphthalenes in contrast with the impossibility of mononitration of 2:6‐ and the difficulty of mononitration of 2:7‐dinitronaphthalene, and also the ease of step‐wise nitration of the other dinitronaphthalenes, are explained on the above theory.