The Sn Mechanism in aromatic compounds. XXIII. Substituent groups attached by saturated sulphur

1958 ◽  
Vol 11 (3) ◽  
pp. 290 ◽  
Author(s):  
NJ Daly ◽  
G Kruger ◽  
J Miller
Keyword(s):  
Nucleophilic Substitution ◽  
Strong Evidence ◽  
Aromatic Compounds ◽  
Aromatic Nucleophilic Substitution

The activating power of p-SMe and p-SMe2+ in aromatic nucleophilic substitution has been compared with available data for ?NH2, -NMe3+, and OMe. The ?Sme2+; group is very powerfully activating and there is strong evidence for a -T effect of ?Sme2+ but not of -SMe, involving expansion of the valency shell beyond an octet. The -SMe group, like -Cl, -Br, and -I, is however also activating, whereas ?NH2, -OMe, and -F are more or less deactivating.

The SN Mechanism in aromatic compounds. 25. Substituent effects of multiple-bond nitrogen.

1958 ◽  
Vol 11 (3) ◽  
pp. 302 ◽  
Author(s):  
J Miller ◽  
AJ Parker
Keyword(s):  
Double Bond ◽  
Nitrogen Atom ◽  
Nucleophilic Substitution ◽  
Benzene Ring ◽  
Aromatic Compounds ◽  
Halogen Atom ◽  
Multiple Bond ◽  
Substituent Effects ◽  
Aromatic Nucleophilic Substitution ◽  
Substituent Constants

The substituent effects in aromatic nucleophilic substitution of groups attached to the benzene ring by a multiple-bond nitrogen atom are considered. Attachment is para to a replaceable halogen atom, and generally as a 4-substituent to l-chloro-2-nitrobenzene. Comparisons with some other groups are shown. Reasons are given for the greater T effect of a triple than of a double bond. Hammett substituent constants (σ*) are computed. Those for the nitroso and diazonium groups .are the largest so far obtained for electrically neutral and cationic groups respectively. The activating power of four of the nitrogen groups in electrophilic as well as nucleophilic substitution is discussed briefly.

ChemInform Abstract: Aromatic Nucleophilic Substitution Reactions of Activated N- Arylpyrazoles with Formamides.

ChemInform ◽  
2010 ◽  
Vol 27 (21) ◽  
pp. no-no
Author(s):  
C. I. CHIRIAC ◽  
V. LUPU ◽  
F. CHIRIAC ◽  
R. ROPOT ◽  
M. TIBIRNA ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reactions ◽  
Aromatic Nucleophilic Substitution ◽  
Nucleophilic Substitution Reactions
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