. Author manuscript; available in PMC: 2015 Jun 3.

Published in final edited form as: Chem Res Toxicol. 2009 Sep;22(9):1499–1508. doi: 10.1021/tx900147g

Table 1.

Calculated Quantum Mechanical Parameters for α,β-Unsaturated Carbonyl Derivatives and Non-Conjugated Analogs

Conjugated alkenes	E_LUMO (ev)	σ (ev^-)	ω (ev)
NEM	−2.36	0.406	4.73
Acrolein	−1.70	0.379	3.57
HNE	−1.53	0.381	3.29
MVK	−1.33	0.372	3.00
MA	−1.01	0.315	2.76
ACR	−0.69	0.329	2.30
Non-conjugated analogs
Propanal	−0.33	0.307	1.98
Allyl alcohol	+0.51	0.269	1.39

The Lowest Unoccupied Molecular Orbital (LUMO) energy (E_LUMO) and Highest Occupied Molecular Orbital (HOMO) energy (E_HOMO), were calculated using Spartan04 (version 1.0.3) software (Wavefunction Inc., Irvine CA). Global (whole molecule) hardness (η) was calculated as η = (E_LUMO-E_HOMO)/2 and softness (σ) was calculated as the inverse of hardness or σ= 1/η. The electrophilicity index (ω) was calculated as ω = μ²/2η, where μ is chemical potential of the electrophile and was calculated as μ = (E_LUMO+E_HOMO)/2 (For details see 42). Abbreviations: NEM = N-ethylmaleimide, HNE = 4-hydroxy-2-nonenal, MVK = methyl vinyl ketone, MA = methyl acrylate and ACR = acrylamide.