Lithium Carbamate/Solvation State Dimer 1→Dimer 2 LiCH2OCON(CH3)2•2Et2O 10.9 LiCH2OCON(CH3)2•3Et2O -3.92 LiCH2OCON(CH3)2•4Et2O 0.800 LiCH2OCON(CH3)2•2THF -10.1 LiCH2OCON(CH3)2•3THF -1.80 LiCH2OCON(CH3)2•4THF -0.0809 LiCHPhOCON(CH3)2•2Et2O RR -0.802 LiCHPhOCON(CH3)2•2Et2O RS -2.01 LiCHPhOCON(CH3)2•2THF RR -1.47 LiCHPhOCON(CH3)2•2THF RS -2.51

Table 5: Relative energies of Dimers 1 and 2 (Dimer 1 → Dimer 2, kcal/mol). Most stable conformation of Dimer 1 compared to most stable conformation of Dimer 2.