29663-54-5

Basic information

• Product Name: TROPYLIUM HEXAFLUOROPHOSPHATE
• Synonyms: TROPYLIUM HEXAFLUOROPHOSPHATE;cycloheptatrienylium,hexafluorophosphate(1-)
• CAS NO: 29663-54-5
• Molecular Formula: C₇H₇*F₆P
• Molecular Weight: 236.09
• EINECS: 249-761-2
• Product Categories: Aromatic Halides (substituted);Carbenium Salts;Building Blocks;Organic Building Blocks
• Mol File: 29663-54-5.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: 0-6°C
• CAS DataBase Reference: TROPYLIUM HEXAFLUOROPHOSPHATE(CAS DataBase Reference)
• NIST Chemistry Reference: TROPYLIUM HEXAFLUOROPHOSPHATE(29663-54-5)
• EPA Substance Registry System: TROPYLIUM HEXAFLUOROPHOSPHATE(29663-54-5)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 29663-54-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H7.F6P/c1-2-4-6-7-5-3-1;1-7(2,3,4,5)6/h1-5H,6H2;/q+1;-1

Upstream product

• 544-25-2 Cyclohepta-1,3,5-triene 

Downstream Products

• 108530-69-4 ReH₂((C₆H₅)2PC₂H₄P(C₆H₅)2)2(CNC₄H₉)⁽¹⁺⁾*PF₆^(1-)={ReH₂((C₆H₅)2PC₂H₄P(C₆H₅)2)2(CNC₄H₉)}PF₆ 
• 108547-90-6 ReH₄(P(C₆H₅)3)4⁽¹⁺⁾*PF₆^(1-)={ReH₄(P(C₆H₅)3)4}PF₆ 
• 108530-79-6 ReH₄(P(C₆H₅)3)3(CNC₆H₃(CH₃)2)⁽¹⁺⁾*PF₆^(1-)={ReH₄(P(C₆H₅)3)3(CNC₆H₃(CH₃)2)}PF₆ 
• 108571-96-6 [ReH₄(PPh₃)₃(NCMe)]PF₆ 
• 108530-77-4 ReH₃(P(C₆H₅)3)3(NCCH₃) 
• 108530-71-8 ReH₂((C₆H₅)2PC₂H₄P(C₆H₅)2)2(NCCH₃)⁽¹⁺⁾*PF₆^(1-)={ReH₂((C₆H₅)2PC₂H₄P(C₆H₅)2)2(NCCH₃)}PF₆ 
• 1399853-15-6 (tetraphenyl-η⁴-cyclobutadiene)(cyclohepta-2′,4′,6′-trien-1′-yl-η⁵-cyclopentadienyl)cobalt(I) 
• 1254075-80-3 2-((2Z,4Z,6Z)-cyclohepta-2,4,6-trienyl)-3-phenylpropanal 
• 421548-18-7 [(1,2-bis(di-tert-butylphosphino)ethane)NiPH(2,6-dimesitylphenyl)][PF₆] 
• 345894-01-1 (1,2-bis(di-tert-butylphosphino)ethane)Ni(NH(2,6-(CH(CH₃)2)2C₆H₃)(PF₆) 

Relevant articles and documents

Charge-transfer structures of aromatic EDA complexes leading to electron transfer with the electrophilic nitrosonium cation

Benzene and hexamethylbenzene partake in the rapid formation of unique electron donor-acceptor (EDA) complexes with the nitrosonium cation, as reflected in the association constants that vary markedly from K = 0.5 to 31000 M-1, respectively. The 1:1 EDA complexes of electron-rich arene donors exhibit particularly high degrees of charge transfer that are established by X-ray crystallography coupled to the infrared spectroscopic analysis of the N-O stretching frequencies. Thus the N-O bond distance undergoes a dramatic lengthening from 0.95 ? in the simple salt NO+SbCl6- to 1.12 ? in the hexamethylbenzene (HMB) complex. Such a bond elongation of the nitrosonium acceptor is equivalent to that extant in nitric oxide (1.15 ?), and it is accompanied by a corresponding change of the aromatic donor in the ground state of the EDA complex to that of the cation radical (HMB.+), as deduced from the changes in the 13C NMR and the IR spectra. The same structural and spectroscopic analysis of the other NO+ complexes reveals a graded series of the EDA complexes in which the degree of charge transfer (Z) varies linearly with the donor strength as measured by the ionization potential of the arene (ArH). The increase of Z from benzene (0.52) to hexamethylbenzene (0.97) in the charge-transfer complex tracks their increasing proclivity to undergo electron transfer and afford arene cation radicals (ArH.+) as reactive intermediates. A general mechanistic formulation based on electron transfer from the charge-transfer complex is developed, in which the facility of the followup reactions (such as fragmentation, cycloreversion, rearrangement, ion-pair annihilation, etc.) of the labile ArH.+ is critical. When the electron transfer is reversible, this 1-electron mechanism is shown not to be readily distinguished from the more conventional electrophilic (2-electron) pathways.