Ethyl lactate: a sinister molecule exhibiting high chemical diversity with potential as a “green” solvent

A comprehensive study of the properties and reactivity of ethyl(S)-lactate has been conducted. The conformational landscape, the enthalpy of formation of the ground state, (Formula presented.) kJ mol⁻¹, the thermochemistry (entropy, specific heat, enthalpy function), adiabatic ionization energy, and the single bond dissociation energies are also mapped out. Unimolecular elimination reactions leading to water and ethyl acrylate or ethene and lactic acid proceed with barriers in excess of 250 kJ mol⁻¹—with the latter always dominant. The chemical kinetics of the abstraction of H-atoms from primary, secondary, tertiary, and alcoholic sites by the radicals H^• and (Formula presented.) are calculated as well as the kinetics of addition reactions to the carbonyl bond.