Benzyl cation

Base Information

• Chemical Name: Benzyl cation
• CAS No.: 6711-19-9
• Molecular Formula: C7H7
• Molecular Weight: 91.1326
• Hs Code.: 2902909090
• DSSTox Substance ID: DTXSID20217411
• Nikkaji Number: J1.158.934K,J416.648E,J325.033D,J1.625.936E
• Wikidata: Q83093927
• Mol file: 6711-19-9.mol

Synonyms:Benzyl cation;6711-19-9;DTXSID20217411

Chemical Property of Benzyl cation

Chemical Property:

• Vapor Pressure: 27.7mmHg at 25°C
• Boiling Point: 110.6°C at 760 mmHg
• Flash Point: 10°C
• PSA: 0.00000
• LogP: 1.87290
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 91.0547752233
• Heavy Atom Count: 7
• Complexity: 42

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [CH2-]C1=CC=CC=C1
• General Description: Methanidylbenzene (benzyl cation) is a reactive carbocation formed during the thermal decomposition of benzyloxychlorocarbene, as demonstrated in the study. The fragmentation process occurs efficiently in acetonitrile, with minimal solvent effects on the reaction kinetics. The formation of the benzyl cation involves intermediates such as ion pairs, and the reaction pathway is influenced by the geometry of the precursor diazirine. While photolytic decomposition can produce benzyl radicals, the primary route under thermal conditions favors carbocation generation, highlighting its stability and relevance in carbene chemistry.

Technology Process of Benzyl cation

There total 36 articles about Benzyl cation which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

NiPF3(1+) (115512-35-1) + benzyl bromide (100-39-0) → NiBr(PF3) + benzylium cation (6711-19-9) + trifluorophosphane (7783-55-3)

Guidance literature:

In gas; byproducts: NiC6H5CH2Br(1+); The react. is performed on an ion cyclotron resonance (ICR) mass spectrometer. The nickel ion and the aromatic compd. are admitted to the ICR cell in approx. 1:1 ratio, to a total pressure of 6E-6 Torr.; MS;

DOI:10.1021/ja00184a007

Reference yield:

Sb2F10 + benzyl fluoride (350-50-5) → benzylium cation (6711-19-9) + antimony pentafluoride (7783-70-2) + [SbF5-(μ-F)-SbF5](1-)

Guidance literature:

In gas; crossed mol. beams, 0.1-1 torr SbF5 in 300-700 torr carrier (He or H2),with decrease of the nozzle temp. from 200°C, increased the Sb2F11(1-) amt.; detected by MS;

DOI:10.1021/ja00407a010

Reference yield:

tert-butyl cation (14804-25-2) + benzyl chloride (100-44-7) → tertiary butyl chloride (507-20-0) + benzylium cation (6711-19-9) + p-benzylbenzyl cation (191232-63-0)

Guidance literature:

With methane; In gaseous matrix; at 30 ℃; Thermodynamic data; Equilibrium constant; Rate constant; various temperature (300-640 K); ΔH₄⁰, ΔS₄⁰, ΔG₄⁰' effect of side reactions;

upstream raw materials:

1-benzyl-2,4,6-trimethyl-pyridinium

tropylium bromide

benzyl bromide

tert-butyl cation

Downstream raw materials:

benzyl chloride

C₈H₈ClO⁽¹⁺⁾

tert-butyl cation

C₈H₉S⁽¹⁺⁾

Refernces

THE FRAGMENTATION OF BENZYLOXYCHLOROCARBENE: FORMATION OF BENZYL CATION

10.1016/S0040-4039(00)96022-2

The study investigates the thermal decomposition of 3-benzyloxy-3-chlorodiazirine in acetonitrile at 25°C to produce benzyloxychlorocarbene, which further fragments to form the benzyl cation. The researchers conducted a detailed analysis of the reaction, examining the effects of different solvents and solvent conditions on the fragmentation process. They found that the reaction proceeded cleanly in acetonitrile, with only minor solvent effects on the rate constant. The study also included an Arrhenius study to determine the energy of activation and a Hammett study to understand the reaction's sensitivity to substituent effects. The researchers proposed that the thermal fragmentation of benzyloxychlorocarbene yields intermediates such as ion pairs and suggested that the geometry of the diazirine prior to decomposition may influence the distribution of these ion pairs. Additionally, they explored the photolytic decomposition of the compound and observed the formation of benzyl radical, although they concluded that this was not the principal pathway for the fragmentation of the carbene. The study was supported by the National Science Foundation and contributed to the understanding of carbene chemistry and the formation of carbocations.

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