The Journal of organic chemistry

Kinetic and thermodynamic stability of naphthalene oxide and related compounds. A comparative microcalorimetric and computational (DFT) study

P Brandt, ZS Jia, A Thibblin

Index: Brandt, Peter; Jia, Zhi Sheng; Thibblin, Alf Journal of Organic Chemistry, 2002 , vol. 67, # 22 p. 7676 - 7682

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Citation Number: 14

Abstract

The kinetics of the acid-catalyzed ring opening of naphthalene 1, 2-oxide (5) in highly aqueous media to give naphthols has been measured by heat-flow microcalorimetry. The reaction enthalpy of this aromatization reaction was measured as Δ H=-51.3±1.7 kcal mol-1. The unexpectedly low reactivity of naphthalene oxide is suggested to be due to an unusually large thermodynamic stability. A crude estimate of the stabilization effect,~ 1 kcal mol-1 ( ...