ISSN:
0020-7608
Keywords:
Computational Chemistry and Molecular Modeling
;
Atomic, Molecular and Optical Physics
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The reaction mechanism of the α, α and α, β elimination of hydrogen fluorides from alkyl fluorides has been studied theoretically. For fluoroethane as a reactant, the transition state (TS) optimized at the level of the 6-31G** basis set shows that the α, β elimination proceeds via a four membered-ring TS with a barrier height 64.6 kcal/mol, while the α, α elimination, via a three-membered ring TS with a 83.7 kcal/mol barrier. Four substituents, CH3, CN, F, and NH2, were used to investigate the substituent effect of elimination by using the 3-21G basis set. The calculated barriers show that NH2-substituted alkyl fluorides favor both the α, α and α, β elimination and these two reactions would be expected to proceed simultaneously. © 1996 John Wiley & Sons, Inc.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
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