Posts Tagged ‘Oxidizing agents’
Thursday, April 4th, 2019
Previously, I explored the Graham reaction to form a diazirine. The second phase of the reaction involved an Sn2′ displacement of N-Cl forming C-Cl. Here I ask how facile the simpler displacement of C-Cl by another chlorine might be and whether the mechanism is Sn2 or the alternative Sn1.
The reason for posing this question is that as an Sn1 reaction, simply ionizing off the chlorine to form a diazacyclopropenium cation might be a very easy process. Why? Because the resulting cation is analogous to the cyclopropenium cation, famously proposed by Breslow as the first example of a 4n+2 aromatic ring for which the value of n is zero and not 1 as for benzene.[1] Another example of a famous “Sn1” reaction is the solvolysis of t-butyl chloride to form the very stable tertiary carbocation and chloride anion (except in fact that it is not an Sn1 reaction but an Sn2 one!)
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References
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R. Breslow, "SYNTHESIS OF THE s-TRIPHENYLCYCLOPROPENYL CATION", Journal of the American Chemical Society, vol. 79, pp. 5318-5318, 1957. http://dx.doi.org/10.1021/ja01576a067
Tags:animation, Carbenium ion, Cations, Chemical elements, chemical reaction, Chemistry, Chlorine, computational chemistry, Cyclopropenium ion, Diazirine, energy, energy profile, free energy, Halogens, Natural sciences, Nucleophilic aromatic substitution, Oxidizing agents, Physical sciences, potential energy surface, SN1 reaction, Substitution reactions
Posted in reaction mechanism | No Comments »
Friday, February 23rd, 2018
A little while ago I pondered allotropic bromine, or Br(Br)3. But this is a far wackier report[1] of a molecule of light.
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References
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Q. Liang, A.V. Venkatramani, S.H. Cantu, T.L. Nicholson, M.J. Gullans, A.V. Gorshkov, J.D. Thompson, C. Chin, M.D. Lukin, and V. Vuletić, "Observation of three-photon bound states in a quantum nonlinear medium", Science, vol. 359, pp. 783-786, 2018. http://dx.doi.org/10.1126/science.aao7293
Tags:Atomic physics, Bromine, Bromine compounds, chemist, Chemistry, Halogens, Hypobromite, Oxidizing agents
Posted in Interesting chemistry | No Comments »
Sunday, November 12th, 2017
A few years back, I took a look at the valence-shell electron pair repulsion approach to the geometry of chlorine trifluoride, ClF3 using so-called ELF basins to locate centroids for both the covalent F-Cl bond electrons and the chlorine lone-pair electrons. Whereas the original VSEPR theory talks about five “electron pairs” totalling an octet-busting ten electrons surrounding chlorine, the electron density-based ELF approach located only ~6.8e surrounding the central chlorine and no “octet-busting”. The remaining electrons occupied fluorine lone pairs rather than the shared Cl-F regions. Here I take a look at ClMe3, as induced by the analysis of SeMe6.
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Tags:Chemical bond, chemical bonding, Chemistry, Chlorine, Covalent bond, Lone pair, Oxidizing agents, Quantum chemistry, Stereochemistry, Valence, VSEPR theory
Posted in Chemical IT, Hypervalency | 5 Comments »
Tuesday, February 14th, 2017
I analysed the bonding in chlorine trifluoride a few years back in terms of VSEPR theory. I noticed that several searches on this topic which led people to this post also included a query about the differences between it and the bromine analogue. For those who posed this question, here is an equivalent analysis.
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Tags:Bromine, Bromine trifluoride, Chemical elements, Chemistry, Chlorine, Fluorides, Halogens, Interhalogen compounds, Matter, Oxidizing agents, VSEPR theory
Posted in Interesting chemistry | 1 Comment »
Friday, April 15th, 2016
If H3N+-O– is viable compared with its tautomer H2N-OH when carrying water bridges, then why not try H2O+-O– vs HO-OH?
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Tags:Ammonia, Anions, free energy, Hydrogen bond, Hydrogen peroxide, Inorganic solvents, Oxide, Oxidizing agents, Peroxide, Properties of water
Posted in General, Interesting chemistry | No Comments »
Sunday, April 26th, 2015
Allotropes are differing structural forms of the elements. The best known example is that of carbon, which comes as diamond and graphite, along with the relatively recently discovered fullerenes and now graphenes. Here I ponder whether any of the halogens can have allotropes.
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Tags:Allotropy, Bromine, Carbon, Chemical elements, Chemistry, free energy barrier, Fullerene, Halogen, Hypobromite, Matter, Nonmetals, Oxidizing agents, Oxygen, pence
Posted in reaction mechanism | 11 Comments »