carbasm.doc 61KB Jun 05 2011 09:30:50 PM

SUPPLEMENTARY MATERIAL

Selected HF/6-31G** geometrical parameters (bond lenghts in Angstroms and bond angles in degrees) for the stable conformers of the compounds of Scheme 1.

1 1TT 1TG 1TG´ 1GT 1GG 1GG´ 1G´T 1G´G 1G´G´

C-O 1.4072 1.3951 1.4030 1.3893

N-C 1.4236 1.4334 1.4314 1.4412

N-C-O 110.95 107.09 115.62 110.17

R4-C-O 110.24 111.25 105.36 105.49

R4-C-N 108.58 108.05 108.70 114.26

R5-C-O 110.25 109.36 110.50 111.45

R5-C-N 108.57 113.56 108.19 107.65

R1-O-C-N 179.89 170.36 69.70 48.34

R2-N-C-O 59.26 -64.95 66.89 -166.75

R3-N-C-O -59.35 173.82 -54.34 71.39

2 2TT 2TG 2TG´ 2GT 2GG 2GG´ 2G´T 2G´G 2G´G´

C-O 1.4019 1.3892 1.4008 1.3856

N-C 1.4228 1.4336 1.4306 1.4425

N-C-O 111.52 107.58 116.19 111.46

R1-O-C 114.18 114.12 115.73 115.22

R4-C-O 109.62 110.71 105.16 105.08

R4-C-N 109.01 108.46 108.64 113.66

R5-C-O 109.62 108.84 109.78 110.75

R5-C-N 109.01 113.85 108.27 107.73

R1-O-C-N 179.99 178.40 72.47 66.78

R2-N-C-O 59.51 -65.46 54.21 -166.57

R3-N-C-O -59.52 173.7 -68.36 71.99

3 3TT 3TG 3TG´ 3GT 3GG 3GG´ 3G´T 3G´G 3G´G´

C-O 1.4127 1.3993 1.4002 1.4082 1.3950 1.4090 1.3944 N-C 1.4285 1.4390 1.4393 1.4361 1.4459 1.4370 1.4460 N-C-O 109.50 105.54 105.39 114.06 108.47 114.04 108.80 R1-O-C 110.20 109.83 109.57 109.82 107.77 109.95 107.83 R4-C-O 109.01 110.21 108.47 104.12 104.52 109.31 110.29 R4-C-N 107.42 107.10 112.37 107.46 112.98 106.97 106.48 R5-C-O 110.87 110.38 111.62 111.12 111.77 106.44 106.80 R5-C-N 110.49 114.61 110.09 110.21 109.97 110.47 115.32 R1-O-C-N -176.35 178.99 -171.28 69.53 48.89 -64.86 -45.70 R2-N-C-O 57.70 -60.80 175.31 51.94 -173.93 65.53 -71.48 R3-N-C-O -60.18 178.78 55.11 -68.48 65.16 -55.04 167.52

4 4TT 4TG 4TG´ 4GT 4GG 4GG´ 4G´T 4G´G 4G´G´

C-O 1.4188 1.4059 1.4150 1.4012

N-C 1.4349 1.4462 1.4426 1.4523

N-C-O 108.15 104.12 112.70 107.32

R1-O-C 110.27 109.70 109.82 107.80

R4-C-O 109.52 110.34 105.07 105.54

R4-C-N 109.00 108.63 108.95 113.74

R5-C-O 109.51 109.13 109.74 110.34

R5-C-N 109.00 113.08 108.75 108.46

R1-O-C-N -179.98 177.91 65.89 46.99

R2-N-C-O 58.68 -54.10 66.68 -173.16

5 5TT 5TG 5TG´ 5GT 5GG 5GG´ 5G´T 5G´G 5G´G´ C-O 1.4085 1.3940 1.3970 1.4042 1.3890 1.3914 1.4047 1.3884 1.3920 N-C 1.4207 1.4313 1.4285 1.4297 1.4417 1.4372 1.4281 1.4393 1.4387 N-C-O 111.30 107.19 108.22 115.64 111.95 110.93 115.83 110.23 112.57 R1-O-C 110.12 109.75 109.71 110.37 110.27 107.85 109.93 107.96 110.31 R3-N-C 115.14 113.89 114.93 115.66 113.34 114.74 115.47 114.39 115.13 R4-C-O 109.99 111.42 109.22 105.62 106.79 105.37 110.33 111.64 109.36 R4-C-N 108.46 108.38 112.59 108.44 108.10 113.41 108.12 107.84 112.02 R5-C-O 110.11 109.87 110.88 110.27 110.04 111.21 105.19 105.90 106.54 R5-C-N 108.56 112.66 108.08 108.28 112.23 107.80 108.76 113.61 108.03 R1-O-C-N 175.33 170.92 -161.87 76.47 75.95 50.46 -69.09 -51.90 -78.87 R2-N-C-O 62.89 -53.26 -161.39 61.34 -60.27 -159.88 70.67 -60.53 -159.84 R3-N-C-O -62.42 -178.19 71.61 -64.54 175.96 73.50 -57.17 174.94 74.19

6 6TT 6TG 6TG´ 6GT 6GG 6GG´ 6G´T 6G´G 6G´G´

C-O 1.4030 1.3912 1.3877 1.4023 1.3846 1.3881 1.3874

N-C 1.4199 1.4284 1.4319 1.4275 1.4404 1.4375 1.4414

N-C-O 111.76 108.54 107.67 116.29 111.32 112.01 113.25

R1-O-C 114.19 114.12 114.24 115.57 115.21 115.12 115.62

R2-N-C 115.17 114.83 113.72 115.56 113.91 114.58 113.89

R4-C-O 109.52 110.43 109.37 104.99 105.66 110.58 109.13

R4-C-N 108.97 108.55 112.93 108.73 113.01 107.94 112.11

R5-C-O 109.44 108.73 110.92 109.65 111.03 104.96 105.97

R5-C-N 108.94 112.85 108.77 108.21 107.95 112.88 108.16

R1-O-C-N -178.31 175.58 -178.95 71.45 69.03 -67.17 -66.58

R2-N-C-O 62.56 -71.98 177.49 56.56 -176.47 -72.91 -157.73

R3-N-C-O -62.95 161.40 52.90 -72.44 59.43 160.41 78.25

7 7TT 7TG 7TG´ 7GT 7GG 7GG´ 7G´T 7G´G 7G´G´

C-O 1.4032 1.3891 1.3858

N-C 1.4206 1.4323 1.4415

N-C-O 111.83 109.07 112.30

R1-O-C 114.18 114.09 115.07

R2-N-C 113.86 112.78 112.36

R3-N-C 113.86 111.93 112.36

R4-C-O 109.40 110.28 105.56

R4-C-N 108.98 108.58 112.21

R5-C-O 109.40 109.27 110.48

R5-C-N 108.98 112.07 108.01

R1-O-C-N 179.99 176.26 68.26

R2-N-C-O 65.45 -64.14 -166.70

R3-N-C-O -65.46 168.01 65.50

8 8TT 8TG 8TG´ 8GT 8GG 8GG´ 8G´T 8G´G 8G´G´

C-O 1.4089 1.3951 1.4046 1.3900 1.3896

N-C 1.4214 1.4325 1.4309 1.4422 1.4408

N-C-O 111.39 108.78 115.67 112.63 111.34

R1-O-C 110.09 109.71 110.27 110.46 108.00 R2-N-C 113.81 112.89 113.67 113.05 112.66 R3-N-C 113.82 112.11 114.20 111.34 112.54 R4-C-O 109.95 110.65 105.43 107.02 105.80 R4-C-N 108.53 108.15 108.61 107.95 112.76 R5-C-O 109.98 109.78 110.21 109.88 111.05 R5-C-N 108.55 111.78 108.25 111.32 107.91

R1-O-C-N 179.21 160.19 74.27 88.84 53.2

R2-N-C-O 65.37 -64.51 62.24 -62.14 -165.25 R3-N-C-O -65.39 167.26 -68.66 170.43 66.75

C-O 1.4139 1.4007 1.4009 1.4098 1.3969 1.3963 1.4098 1.3954 1.3958 N-C 1.4259 1.4413 1.4378 1.4354 1.4517 1.4462 1.4333 1.4474 1.4485 N-C-O 109.82 105.02 106.57 114.16 109.40 109.43 114.34 107.79 110.79 R1-O-C 110.23 109.79 109.85 110.34 110.18 107.81 109.78 108.05 110.34 R3-N-C 115.22 115.32 117.52 115.85 115.29 117.29 115.52 116.23 117.72 R4-C-O 110.57 111.10 110.34 106.51 107.23 106.63 110.87 111.22 110.40 R4-C-N 110.48 111.64 115.75 110.38 111.29 116.70 110.20 111.91 115.38 R5-C-O 108.98 108.97 109.80 109.14 109.20 110.01 104.02 104.85 105.41 R5-C-N 107.38 111.11 105.95 106.99 110.54 105.55 107.48 111.95 105.84 R1-O-C-N 172.44 176.83 -172.68 71.78 79.96 47.54 -69.23 -55.53 -82.89 R2-N-C-O 62.69 -36.43 -164.52 61.95 -33.24 -160.42 71.39 -49.97 -166.35 R3-N-C-O -62.05 -160.27 66.26 -63.68 -158.21 70.70 -55.90 -172.98 65.30

10 10TT 10TG 10TG´ 10GT 10GG 10GG´ 10G´T 10G´G 10G´G´