22374-73-8

Basic information

• Product Name: indole nitranion
• Synonyms: indole nitranion
• CAS NO: 22374-73-8
• Molecular Weight: 116.142
• Mol File: 22374-73-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: indole nitranion(CAS DataBase Reference)
• NIST Chemistry Reference: indole nitranion(22374-73-8)
• EPA Substance Registry System: indole nitranion(22374-73-8)

Safety Data

• Hazardous Substances Data: 22374-73-8(Hazardous Substances Data)

Upstream product

• 120-72-9 indole 
• 98-95-3 nitrobenzene radical anion 
• 71-50-1 acetate 

Relevant articles and documents

Ionic Probes of Aromaticity in Annelated Rings

Ionization by the deprotonation of benzene and pyridine, and by the protonation of pyridine, involves lone pairs in the ? plane without significant ? effects.In these cases annelation by a benzene ring increases the acidity or proton affinity by a constant 6+/-1 kcal/mol, ascribed to increased polarizability.In comparison, protonation of benzene and deprotonation of cyclopentadiene disrupts or creates a 6-electron aromatic system, respectively, and in their annelated derivatives, naphthalene and indene, a secondary 4-electron conjugated ? system.These cases involving ? electrons show annelation effects that are substantially larger (13.4 kcal/mol) or smaller (1.0 kcal/mol), respectively, than just the electrostatic effect.Analysis of these data suggests that the stability of secondary 4-electron system in the annelated rings is smaller by 6+/-1 kcal/mol than the aromatic 6-electron systems, in fair agreement with Herndon's structure-resonance values for these species.Annelation effects are reproduced well by Dewar's AM1 semiempirical method.