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. Author manuscript; available in PMC: 2011 May 13.
Published in final edited form as: J Phys Chem A. 2010 May 13;114(18):5913–5918. doi: 10.1021/jp101329f

Table 1.

SN2 energy barrier heights for 59 systems investigated in this study together with their energy decomposition analyses based on Eqs. (1) and (3). For the comparison purpose, the steric energy difference from the NBO analysis is also tabulated for the systems. Units are in kcal/mol.

Models (R1R2R3) ΔE ΔEs ΔEq ΔEe ΔTs ΔExc Δ(NBOSteric)
HHH 9.22 89.40 −93.73 13.56 −22.84 18.50 −30.17
CH3HH 14.67 122.83 −130.24 22.08 −27.92 20.51 −15.58
CH3CH3H 19.66 145.01 −155.68 30.33 −35.80 25.12 −17.15
CH3CH3CH3 27.13 148.69 −161.12 39.55 −40.53 28.10 −7.15
PhCH3CH3 29.42 158.89 −168.47 39.00 −38.99 29.41 −27.96
C2H5C2H5C2H5 24.90 126.99 −136.16 34.06 −37.23 28.07 −0.92
C2H5C2H5CH3 25.52 134.71 −144.12 34.92 −37.98 28.57 −11.23
C2H5CH3CH3 26.21 139.65 −150.60 37.15 −39.22 28.27 −9.40
PhPhCH3 30.75 154.87 −166.14 42.03 −42.89 31.62 −23.87
PhPhPh 24.48 150.45 −160.59 34.62 −43.22 33.08 −52.53
PhCH3H 21.66 170.70 −178.00 28.96 −34.16 26.87 −27.65
PhHH 16.36 161.63 −170.21 24.93 −32.82 24.25 −10.39
C2H5HH 13.79 118.08 −125.34 21.05 −27.67 20.41 2.60
C3H8C2H5C2H5 24.84 126.33 −135.31 33.82 −37.06 28.08 −1.67
C3H8C3H8C2H5 26.80 108.45 −119.76 38.11 −39.46 28.15 −4.42
C3H8C3H8C3H8 26.69 106.40 −118.04 38.33 −39.70 28.06 −6.39
CCl3HH 18.98 9.08 −8.21 18.11 −18.11 18.99 5.13
CF3CH3H 20.93 90.78 −99.76 29.91 −32.06 23.08 −42.65
CF3HH 17.28 89.53 −98.54 26.29 −27.97 18.96 −28.41
ClClCl 13.05 −5.54 0.12 18.47 −31.60 26.18 −93.70
ClClH 32.43 32.34 −55.72 55.81 −36.52 13.14 −44.86
ClHH 20.40 85.25 −97.26 32.41 −29.52 17.51 −32.41
FClCl 13.31 −20.49 14.76 19.04 −29.09 23.36 −98.20
FFCl 14.19 −41.23 32.61 22.81 −28.13 19.50 −97.11
FFF 15.94 −61.09 49.61 27.43 −27.12 15.64 −64.78
FFH 28.80 14.14 −34.51 49.18 −37.73 17.35 −19.86
FHH 17.15 70.32 −80.97 27.80 −29.37 18.72 −13.49
OCH3FH 25.35 25.67 −42.07 41.76 −35.27 18.87 −7.90
OCH3HH 19.01 116.61 −127.03 29.43 −33.06 22.64 7.07
OHFF 74.78 49.10 −81.88 107.56 −62.89 30.12 −24.67
OHHH 38.98 231.56 −241.01 48.43 −34.06 24.60 39.86
OHOHH 34.38 127.41 −138.82 45.79 −25.27 13.85 22.60
p-Ph(CCH)CH3H 20.87 168.74 −175.35 27.48 −33.14 26.52 −25.42
p-Ph(CCH)HH 8.32 98.10 −99.58 9.79 −18.41 16.94 −6.23
p-Ph(CH3)CH3H 21.73 171.60 −179.70 29.82 −35.09 26.99 −25.89
p-Ph(CH3)HH 16.47 162.07 −170.01 24.41 −32.12 24.17 −10.33
p-Ph(CN)CH3H 20.33 166.21 −172.50 26.62 −31.90 25.61 −24.90
p-Ph(CN)HH 8.87 114.41 −114.39 8.85 −16.81 16.83 −0.85
p-Ph(Cl)CH3H 21.82 169.25 −177.44 30.00 −34.16 25.97 −25.35
p-Ph(Cl)HH 16.61 162.14 −171.20 25.67 −32.47 23.40 −9.33
p-Ph(F)CH3H 22.06 171.41 −179.11 29.77 −34.20 26.50 −26.78
p-Ph(F)HH 16.81 160.44 −169.92 26.29 −33.24 23.76 −8.50
p-Ph(NH2)CH3H 22.51 179.26 −186.69 29.94 −34.92 27.49 −22.16
p-Ph(NH2)HH 17.18 161.93 −170.73 25.98 −32.96 24.16 −1.00
p-Ph(NO2)CH3H 19.31 161.15 −168.39 26.55 −32.01 24.77 −32.81
p-Ph(NO2)HH 1.53 39.39 −33.55 −4.30 5.38 0.45 26.40
p-Ph(OCH3)CH3H 23.83 213.73 −218.29 28.39 −34.90 30.34 −28.18
p-Ph(OCH3)HH 18.58 198.18 −204.76 25.16 −33.66 27.09 −3.51
p-Ph(OH)CH3H 22.96 177.50 −185.49 30.95 −35.41 27.42 −20.94
p-Ph(OH)HH 17.69 160.60 −170.22 27.31 −33.71 24.09 −8.68
m-Ph(CCH)HH 16.69 162.38 −171.31 25.63 −33.24 24.30 −5.73
m-Ph(CH3)HH 16.72 162.60 −171.73 25.85 −33.43 24.30 −7.66
m-Ph(CN)HH 16.57 163.93 −172.32 24.96 −32.48 24.09 −12.21
m-Ph(Cl)HH 16.36 161.20 −170.71 25.86 −33.57 24.07 −11.04
m-Ph(F)HH 16.21 162.07 −170.57 24.70 −32.44 23.94 −12.59
m-Ph(NH2)HH 29.37 247.74 −256.66 38.29 −35.94 27.02 10.45
m-Ph(NO2)HH 16.69 162.80 −172.22 26.11 −33.79 24.37 −9.59
m-Ph(OCH3)HH 20.07 176.82 −187.73 30.99 −36.02 25.11 −0.32
m-Ph(OH)HH 16.52 162.71 −171.26 25.07 −32.69 24.14 −12.11