The Friedel-​Crafts acetylation of naphthalene.  Evidence for concurrent second- and third-​order reactions

Fadhil S. Kamounah; Andreas D. Andreou; Roger V. Bulbulian; P.H. Gore; A.Y. Miri; David N.  Waters

doi:10.1039/P29810000376

The Friedel-Crafts acetylation of naphthalene. Evidence for concurrent second- and third-order reactions

Fadhil S. Kamounah, Andreas D. Andreou, Roger V. Bulbulian, P.H. Gore, A.Y. Miri, David N. Waters

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

The Friedel–Crafts acetylation of naphthalene has been shown to give varying α : β isomer ratios as a function of concentration of the reactants. In consequence the ratio is strongly time- and temperature-dependent. Values of the α : β ratio (determined by an extrapolation procedure, for 1,2-dichloroethane solution) for the limit of zero reaction time, were plotted against reactant concentration, to give a straight line having a near-zero intercept. From this it is inferred that, whereas β-acetylation is essentially first-order with respect to the acylating reagent, α-acetylation is dominantly second-order in acylating reagent.

Original language	English
Article number	55
Journal	Journal of the Chemical Society. Perkin Transactions 2 (2001)
Volume	2
Pages (from-to)	376-378
Number of pages	3
ISSN	1472-779X
DOIs	https://doi.org/10.1039/P29810000376
Publication status	Published - 1981
Externally published	Yes

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10.1039/P29810000376

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title = "The Friedel-Crafts acetylation of naphthalene. Evidence for concurrent second- and third-order reactions",

abstract = "The Friedel–Crafts acetylation of naphthalene has been shown to give varying α : β isomer ratios as a function of concentration of the reactants. In consequence the ratio is strongly time- and temperature-dependent. Values of the α : β ratio (determined by an extrapolation procedure, for 1,2-dichloroethane solution) for the limit of zero reaction time, were plotted against reactant concentration, to give a straight line having a near-zero intercept. From this it is inferred that, whereas β-acetylation is essentially first-order with respect to the acylating reagent, α-acetylation is dominantly second-order in acylating reagent.",

author = "Kamounah, {Fadhil S.} and Andreou, {Andreas D.} and Bulbulian, {Roger V.} and P.H. Gore and A.Y. Miri and Waters, {David N.}",

year = "1981",

doi = "10.1039/P29810000376",

language = "English",

volume = "2",

pages = "376--378",

journal = "Royal Chemical Society. Journal. Perkin Transactions 2",

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T1 - The Friedel-Crafts acetylation of naphthalene. Evidence for concurrent second- and third-order reactions

AU - Kamounah, Fadhil S.

AU - Andreou, Andreas D.

AU - Bulbulian, Roger V.

AU - Gore, P.H.

AU - Miri, A.Y.

AU - Waters, David N.

PY - 1981

Y1 - 1981

N2 - The Friedel–Crafts acetylation of naphthalene has been shown to give varying α : β isomer ratios as a function of concentration of the reactants. In consequence the ratio is strongly time- and temperature-dependent. Values of the α : β ratio (determined by an extrapolation procedure, for 1,2-dichloroethane solution) for the limit of zero reaction time, were plotted against reactant concentration, to give a straight line having a near-zero intercept. From this it is inferred that, whereas β-acetylation is essentially first-order with respect to the acylating reagent, α-acetylation is dominantly second-order in acylating reagent.

AB - The Friedel–Crafts acetylation of naphthalene has been shown to give varying α : β isomer ratios as a function of concentration of the reactants. In consequence the ratio is strongly time- and temperature-dependent. Values of the α : β ratio (determined by an extrapolation procedure, for 1,2-dichloroethane solution) for the limit of zero reaction time, were plotted against reactant concentration, to give a straight line having a near-zero intercept. From this it is inferred that, whereas β-acetylation is essentially first-order with respect to the acylating reagent, α-acetylation is dominantly second-order in acylating reagent.

U2 - 10.1039/P29810000376

DO - 10.1039/P29810000376

M3 - Journal article

VL - 2

SP - 376

EP - 378

JO - Royal Chemical Society. Journal. Perkin Transactions 2

JF - Royal Chemical Society. Journal. Perkin Transactions 2

SN - 1472-779X

M1 - 55

ER -

The Friedel-​Crafts acetylation of naphthalene. Evidence for concurrent second- and third-​order reactions

Abstract

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Cite this

The Friedel-Crafts acetylation of naphthalene. Evidence for concurrent second- and third-order reactions