The energetics of naphthalene derivatives. II. The isomeric 1— and 2—naphthyl acetates

Abstract

The isomeric 1- and 2-naphthyl acetates (acetoxynaphthalenes) are at the confluence of diverse concepts, techniques and classes of organic compounds. Summing the results of literature measurements of the enthalpy of formation of their solids and of our new sublimation enthalpies reported herein, we derive gas phase enthalpies of formation of −209.9 ± 1.4 and −213.3 ± 1.3 kJ mol−1 respectively. This corresponds to 2-naphthyl acetate being more stable than its 1-isomer by 3.4 ± 1.9 kJ mol−1. We also performed MP2(full)/6-31G(d) calculations on these species, resulting in enthalpies of formation of −212.9 ± 3.9 and −212.2 ± 3.9 kJ mol−1 for 1- and 2-naphthyl acetate and a difference of −0.7 kJ mol−1 respectively in satisfactory agreement with the above experimental results.