Aggregate Conformation 1→2 Conformation 2→3 LiCH2OCON(CH3)2m -23.7 N/A LiCH2OCON(CH3)2d1 -21.6 1.92 LiCH2OCON(CH3)2d2 -5.29 0.764 LiCHPhOCON(CH3)2m -25.0 N/A LiCHPhOCON(CH3)2d1-RR -2.15 1.52 LiCHPhOCON(CH3)2d1-RS -2.36 2.72 LiCHPhOCON(CH3)2d2-RR -14.0 11.4 LiCHPhOCON(CH3)2d2-RS -13.8 10.2

Table 1: Relative free energies (kcal/mol) of N-lithium and O-lithium coordination of lithium carbamate monomers and dimers.