2000
DOI: 10.1002/(sici)1521-3773(20000103)39:1<125::aid-anie125>3.0.co;2-r
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Thermochemical Data of Organic Ions Obtained from Investigations in the More or Less “Diluted” Gas Phase

Abstract: How is a proton bound to an arene, how mobile is it in such a complex, and how much energy is required to remove it-these questions have been of fundamental interest in physical organic chemistry for half a century. The experimental determination of quantitative thermochemical data of organic elementary processes in the gas phase is discussed for recent examples, such as the alpha-acidification of tertiary amines by complexation with boranes (see reaction) and the "local" C(alpha)-H acidities of alpha,alpha,al… Show more

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Cited by 38 publications
(3 citation statements)
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“…+ at low temperature is the σ -complex (1) having a C 2v planar structure. [5][6][7][8] The experimental proton affinity of C 6 H 6 fits well with the theoretical value for the formation of (1), supporting that C 6 H 7…”
Section: Introductionsupporting
confidence: 75%
“…+ at low temperature is the σ -complex (1) having a C 2v planar structure. [5][6][7][8] The experimental proton affinity of C 6 H 6 fits well with the theoretical value for the formation of (1), supporting that C 6 H 7…”
Section: Introductionsupporting
confidence: 75%
“…NMR spectra of C 6 H 7 + in superacid indicate that the most stable conformer of C 6 H 7 + at low temperature is the σ -complex (1) having a C 2v planar structure. [5][6][7][8] The experimental proton affinity of C 6 H 6 fits well with the theoretical value for the formation of (1), supporting that C 6 H 7 + exists as a σ -complex. [9][10][11][12] Quantumchemical computations also support this assignment and predict that the bridged π -complex (2) is a transition state for a 1,2-H shift within (1) and that the face-centered π complex (3) is a second-order saddle point.…”
Section: Introductionsupporting
confidence: 75%
“…The equilibrium shifts to the right-hand side in the HA ⇌ H + + A – mean that the HA can be the strong acid and the A – is the stable conjugate base. Recently, efforts have been laid in the design of potential neutral organic superacids. Polycyanated hydrocarbon derivatives have been designed and examined, which behave as hyperacids. , The parent hydrocarbons of such polycyanated hydrocarbons exhibit tautomerism, which results in a large number of tautomers. Some of these tautomers are less stable and possess lower acidity.…”
Section: Introductionmentioning
confidence: 99%