Aggregate Conformation 1→2 Conformation 2→3
LiCH2OCON(CH3)2m•2Et2O -20.7 N/A
LiCH2OCON(CH3)2m•3Et2O -17.0 N/A
LiCH2OCON(CH3)2m•2THF -18.3 N/A
LiCH2OCON(CH3)2m•3THF -16.6 N/A
LiCH2OCON(CH3)2d1•2Et2O -21.6 1.92
LiCH2OCON(CH3)2d1•3Et2O 3.70 -9.73
LiCH2OCON(CH3)2d1•4Et2O 3.90 -6.67
LiCH2OCON(CH3)2d1•2THF 4.77 -13.9
LiCH2OCON(CH3)2d1•3THF 11.2 -9.75
LiCH2OCON(CH3)2d1•4THF 8.35 -8.63
LiCH2OCON(CH3)2d2•2Et2O 0.858 -13.3
LiCH2OCON(CH3)2d2•3Et2O 2.92 -12.5
LiCH2OCON(CH3)2d2•4Et2O 6.97 -7.94
LiCH2OCON(CH3)2d2•2THF -22.3 11.2
LiCH2OCON(CH3)2d2•3THF 16.6 -16.2
LiCH2OCON(CH3)2d2•4THF 0.972 -4.46
LiCHPhOCON(CH3)2m•2Et2O -21.7 N/A
LiCHPhOCON(CH3)2m•3Et2O -19.5 N/A
LiCHPhOCON(CH3)2m•2THF -19.5 N/A
LiCHPhOCON(CH3)2m•3THF -20.1 N/A
LiCHPhOCON(CH3)2d1 RR•2Et2O 4.06 1.54
LiCHPhOCON(CH3)2d1 RR•2THF 4.79 -0.176
LiCHPhOCON(CH3)2d1 RS•2Et2O -5.99 -1.43
LiCHPhOCON(CH3)2d1 RS•2Et2O 2.53 -6.45
LiCHPhOCON(CH3)2d2 RR•2Et2O -9.84 1.47
LiCHPhOCON(CH3)2d2 RR•2THF -8.24 5.29
LiCHPhOCON(CH3)2d2 RS•2Et2O -14.0 4.76
LiCHPhOCON(CH3)2d2 RS•2Et2O -10.2 3.55
Table 4: Relative free energies (kcal/mol) of N-lithium and O-lithium coordination of lithium carbamate monomers and dimers in diethyl ether and THF.