The thermal decomposition of 2-chloroethanol

Skingle, DC; Stimson, VR

doi:10.1071/ch9760609

Cited by 17 publications

(13 citation statements)

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“…In order to compensate for these effects, the flux of the 2-CLE molecules was gradually increased with temperature, being about 50% larger at 600 K than at 300 K. At the cell temperature of about 650 K we observed a sudden increase in the pressure in the vacuum chamber and simultaneous decrease in the intensity of the spectrum, which are ascribed to decomposition of the 2-CLE molecules in agreement with previous reports. 15 In the spectral range of 2800-3050 cm −1 bands at 2885.4, 2935.5, 2971.8, and 3015.6 cm −1 have been observed, which are assigned to CH 2 symmetric and antisymmetric stretches of CH 2 OH and CH 2 Cl groups of the 2-CLE molecules. An additional band at 2957.6 cm −1 remains unassigned.…”

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confidence: 87%

Using He droplets for measurements of interconversion enthalpy of conformers in 2-chloroethanol

Skvortsov

Vilesov

2009

The Journal of Chemical Physics

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2-chloroethanol molecules having temperature from 300 to 600 K have been captured by helium droplets and the infrared spectra of the O–H and C–H stretching bands of the embedded molecules have been obtained. The intensity ratio of the bands due to trans and gauche conformers of the molecules follows the Arrhenius dependence, giving the enthalpy of conformers interconversion of 1.1 kcal/mol. It is concluded that the abundance ratio of the conformers, which are at equilibrium in the gas phase, remains unchanged upon the rapid cooling of the molecules in the helium droplets.

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confidence: 87%

Using He droplets for measurements of interconversion enthalpy of conformers in 2-chloroethanol

Skvortsov

Vilesov

2009

The Journal of Chemical Physics

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“…Wagner-Meerwein rearrangements have been proposed in the gas phase pyrolysis of neopentyl chloride [I] and bromide [2], bornyl [3] and isobornyl [4] chlorides, 2-chloroethanol [5], and neopentyl chloroformate [6].…”

Section: Introductionmentioning

confidence: 99%

Evidence for α‐elimination from neopentyl chloride in the gas phase

Failes

Mollah

Shapiro

1979

Int J of Chemical Kinetics

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Experimental evidence is presented for a unimolecular gas-phase Wagner-Meerwein shift in neopentyl chloride pyrolysis. In the decomposition of a,a-neopentyl chloride-dz at 445'C, maximally inhibited by cyclohexene, the initial products were isotopically pure 2-methyl-1-butene-dz and 2-methyl-2-butene-dI. Rearrangement, accompanied by loss of either aor y-hydrogen in the formation of hydrogen chloride, is consistent with an incipient ion-pair type of transition state. The cyclohexene maximally inhibited pyrolysis of neopentyl chloride was also examined over the temperature range 424478°C and Arrhenius parameters of E , 258.7 kJ/mole and logA/sec-', 13.78, were determined.

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“…This substrate cannot dehydrochlorinate through a fourmembered cyclic transition state as in most alkyl halides, because of the lack of an adjacent 6-hydrogen (1). An intramolecular migration or rearrangement may be expected (2), or the elimination of HCI could take place through a six-centred state mechanism (3).…”

Section: Introductionmentioning

confidence: 99%