Supplementary material to:
Ab Initio and Density Functional Theory Study of Structures and Energies for Dimethoxymethane as a Model for the Anomeric Effect John R. Kneisler and Norman L. Allinger
[image:1.612.36.515.162.755.2]Journal of Computational Chemistry 17(7) 757-766
Table 5
MP2/6-31g** Structral Parameters and Energies for DMM Torsion Angle 180
Angle C1-O2* O2-C3 C3-O4 O4-C5 C1O2C3 O2C3O4 C3O4C5 Energy 0 1.4247 1.4045 1.4088 1.418 116.7559 111.1871 110.9413 268.74847 30 1.4253 1.3977 1.4102 1.4176 114.9021 110.8640 110.9954 268.75233 60 1.4255 1.3874 1.4135 1.4169 112.2053 109.7266 111.1202 268.75726 90 1.4238 1.3891 1.4135 1.4171 112.6213 108.8518 110.9689 268.75501 120 1.4208 1.3955 1.4082 1.4174 113.7058 107.4191 110.8682 268.75067 150 1.4184 1.398 1.401 1.4175 112.3781 105.9475 110.9531 268.75028 180 1.4177 1.3976 1.3975 1.4177 111.0112 105.5499 111.0107 268.75131 Torsion Angle 150
0 1.4241 1.4089 1.4094 1.4192 116.6857 111.6373 112.416 268.74744 30 1.4243 1.4017 1.4107 1.4185 114.936 111.2824 112.6566 268.75147 60 1.4243 1.3908 1.4147 1.418 112.2005 110.1494 112.7306 268.75649 90 1.4223 1.3925 1.4153 1.4185 112.502 109.346 112.6414 268.75367 120 1.4199 1.3999 1.4104 1.4181 113.6853 108.1382 112.4534 268.74856 150 1.4179 1.4024 1.4025 1.4179 112.3002 106.5627 112.3022 268.74841 180 1.4175 1.401 1.398 1.4184 110.9518 105.9463 112.3793 268.75028 Torsion Angle 120
0 1.4222 1.4177 1.4073 1.4221 116.2084 113.1561 113.8616 268.74769 30 1.4219 1.4106 1.4089 1.4213 114.7858 112.9686 114.0973 268.75116 60 1.4213 1.3984 1.4133 1.4211 112.2003 112.0277 114.1721 268.7558 90 1.4212 1.3994 1.4134 1.421 113.311 111.7494 114.1657 268.75281 120 1.4201 1.4077 1.4078 1.4201 113.9323 110.1415 113.9376 268.74825 150 1.418 1.4104 1.3999 1.4199 112.451 108.135 113.687 268.74856 180 1.4174 1.4083 1.3955 1.4208 110.8665 107.4154 113.7025 268.75067 Torsion Angle 90
0 1.4201 1.4252 1.4004 1.4262 117.0222 115.5966 113.4082 268.74983 30 1.4172 1.4169 1.4033 1.4242 116.3388 116.5455 115.9435 268.75104 60 1.4182 1.4048 1.4067 1.4224 114.5182 116.2886 116.4242 268.75474 90 1.4213 1.4052 1.4051 1.4212 115.0019 114.9208 115.0069 268.75468 120 1.421 1.4133 1.3994 1.4212 114.1446 111.7485 113.2937 268.75281 150 1.4185 1.4153 1.3924 1.4224 112.6034 109.2823 112.4518 268.75367 180 1.4171 1.4139 1.3889 1.4239 110.9729 108.8462 112.611 268.75501 Torsion Angle 60
0 1.4173 1.4242 1.4022 1.4271 120.1066 119.3928 116.3005 268.74427 30 1.4142 1.4186 1.4065 1.421 121.2395 121.3368 118.7133 268.74283 60 1.4176 1.4084 1.4083 1.4175 118.5174 120.2716 118.5113 268.74894 90 1.4222 1.4067 1.4048 1.4182 116.4408 116.3213 114.5426 268.75474 120 1.4211 1.4133 1.3985 1.4213 114.1755 112.0373 112.2134 268.7558 150 1.4182 1.4148 1.3909 1.4241 112.7705 110.1448 112.148 268.75649 180 1.4169 1.4135 1.3875 1.4255 111.1221 109.7435 112.2172 268.75726 Torsion Angle 30
90 1.4242 1.4033 1.4169 1.4172 115.9344 116.5428 116.3317 268.75104 120 1.4212 1.4088 1.4106 1.4219 114.0938 112.9774 114.7955 268.75116 150 1.4186 1.4108 1.4016 1.4243 112.6655 111.2843 114.9306 268.75147 180 1.4178 1.4105 1.3975 1.4254 110.9881 110.8696 114.8796 268.75232 Torsion Angle 0
0 1.4142 1.4222 1.4219 1.4142 125.886 124.91 125.865 268.72431 30 1.4183 1.4153 1.4230 1.4144 122.545 123.681 124.759 268.73063 60 1.427 1.4023 1.424 1.4173 116.297 119.363 120.100 268.74427 90 1.4262 1.4011 1.4245 1.4204 113.400 115.535 116.990 268.74983 120 1.4222 1.407 1.4181 1.4222 113.860 113.159 116.224 268.74769 150 1.4193 1.4094 1.4089 1.4241 112.421 111.650 116.702 268.74744 180 1.4181 1.4085 1.4047 1.4247 110.953 111.175 116.730 268.74847 Torsion Angle 30
0 1.4148 1.4230 1.4154 1.4183 124.721 123.693 122.567 268.73063 30 1.4232 1.4149 1.4144 1.4232 119.383 120.501 119.314 268.74094 60 1.4317 1.4026 1.4169 1.4246 113.338 115.749 115.086 268.75362 90 1.4257 1.4029 1.4153 1.4226 112.653 114.196 113.888 268.75577 120 1.4223 1.4097 1.4097 1.4233 113.753 112.895 114.275 268.75144 150 1.4189 1.4117 1.4016 1.4248 112.196 111.349 114.685 268.75103 180 1.4177 1.4103 1.3977 1.4253 111.007 110.873 114.901 268.75233 Torsion Angle 60
0 1.4173 1.4242 1.4022 1.4271 120.107 119.393 116.301 268.74427 30 1.4246 1.4168 1.4027 1.4318 115.085 115.760 113.354 268.75362 60 1.4252 1.405 1.4048 1.4250 111.868 113.809 111.827 268.76272 90 1.4240 1.4069 1.4041 1.4234 112.487 113.204 111.736 268.76038 120 1.4204 1.4135 1.3983 1.4237 113.629 111.793 111.787 268.75591 150 1.4176 1.415 1.3911 1.4252 112.275 110.262 112.036 268.75572 180 1.4169 1.4134 1.3877 1.4257 111.126 109.786 112.284 268.75726 Torsion Angle 90
0 1.4204 1.4243 1.4013 1.4261 116.997 115.525 113.3858 268.74983 30 1.4224 1.4150 1.4031 1.4257 113.899 114.220 112.652 268.75577 60 1.4235 1.4042 1.4067 1.424 111.760 113.203 112.4669 268.76038 90 1.4220 1.4059 1.4058 1.4219 112.546 112.540 112.5301 268.75749 120 1.4192 1.4127 1.3996 1.4225 113.645 111.142 112.8640 268.75314 150 1.4172 1.4143 1.3923 1.4239 112.264 109.503 112.9073 268.75346 180 1.4171 1.4135 1.3890 1.4238 110.965 108.843 112.6238 268.75501 Torsion Angle 120
0 1.4222 1.4177 1.4073 1.4221 116.208 113.156 113.864 268.74769 30 1.4233 1.4097 1.4097 1.4223 114.273 112.892 113.746 268.75144 60 1.4220 1.3969 1.4118 1.4188 111.799 111.811 113.659 268.75591 90 1.4209 1.3984 1.4108 1.4177 112.911 111.144 113.680 268.75314 120 1.4200 1.4061 1.4062 1.4200 113.796 109.467 113.808 268.74934 150 1.4181 1.4086 1.3985 1.4212 112.387 107.838 113.882 268.74976 180 1.4174 1.4083 1.3955 1.4208 110.867 107.415 113.703 268.75067 Torsion Angle 150
0 1.4241 1.4089 1.4094 1.4192 116.688 111.637 112.416 268.74744 30 1.4248 1.4018 1.4117 1.4190 114.717 111.364 112.190 268.75103 60 1.4253 1.3912 1.4147 1.4175 112.064 110.259 112.239 268.75572 90 1.4239 1.3924 1.4143 1.4172 112.910 109.509 112.267 268.75346 120 1.4212 1.3985 1.4086 1.4181 113.882 107.841 112.389 268.74976 150 1.4187 1.4010 1.4010 1.4187 112.471 106.199 112.473 268.74970 180 1.4175 1.4010 1.3980 1.4184 110.952 105.946 112.380 268.75028 Torsion Angle 180
60 1.4255 1.3874 1.4135 1.4169 112.205 109.727 111.120 268.75726 90 1.4238 1.3891 1.4135 1.4171 112.621 108.852 110.969 268.75501 120 1.4208 1.3955 1.4082 1.4174 113.706 107.419 107.419 268.75067 150 1.4184 1.3980 1.4010 1.4175 112.378 105.948 105.948 268.75028 180 1.4177 1.3976 1.3975 1.4177 111.011 105.550 105.550 268.75131 Bond lengths are in Å, bond angles are in degrees, and energies are in Hartrees.
[image:3.612.44.560.191.758.2]*See Figure 1a for atom numberings.
Table 6
DFT-Becke3LYP/6-31g** Structural Parameters for DMM Torsion Angle 180
Angle C1-O2* O2-C3 C3-O4 O4-C5 C1O2C3 O2C3O4 C3O4C5 Energy 0 1.4216 1.4018 1.4067 1.4133 118.0578 111.6085 112.3958 269.54982 30 1.4224 1.3949 1.4088 1.4125 116.3632 111.2301 112.4769 269.55331 60 1.4231 1.3856 1.413 1.4122 113.7639 110.2359 112.4847 269.55798
90 1.4206 1.3864 1.4135 1.4121 114.3292 109.2259 112.37 269.55631
120 1.4168 1.3929 1.4078 1.4121 115.2138 107.7549 112.2949 269.55242 150 1.4134 1.3956 1.3997 1.4126 113.9967 106.3284 112.2934 269.55202 180 1.4128 1.3957 1.3957 1.4128 112.427 105.9705 112.4279 269.55294 Torsion Angle 150
0 1.4207 1.4065 1.4074 1.4142 117.8969 111.9453 114.0227 269.54885
30 1.4211 1.3995 1.409 1.4139 116.496 111.7039 114.191 269.55248
60 1.4211 1.3893 1.4141 1.4136 113.9674 110.6463 114.2906 269.5572
90 1.4192 1.3904 1.415 1.4136 114.3014 109.7155 114.3024 269.555
120 1.416 1.398 1.4096 1.4133 115.1588 108.4405 113.9395 269.55045 150 1.4128 1.4007 1.4007 1.4128 113.8919 106.8703 113.8756 269.55025 180 1.4126 1.3997 1.3957 1.4135 112.3011 106.3269 113.928 269.55202 Torsion Angle 120
0 1.4185 1.4161 1.4048 1.4183 117.5334 113.5848 115.3371 269.54886 30 1.4185 1.4092 1.407 1.4176 116.4086 113.4111 115.4436 269.55196
60 1.4184 1.3976 1.4124 1.4175 114.013 112.5168 115.5229 269.5563
90 1.4182 1.398 1.4125 1.4171 114.9184 112.0911 115.6108 269.55415 120 1.4166 1.407 1.4071 1.4167 115.411 110.5168 115.3513 269.55009 150 1.4134 1.4096 1.3981 1.416 113.9298 108.456 115.2709 269.55044 180 1.4123 1.4077 1.3932 1.417 112.3017 107.7398 115.1261 269.55242 Torsion Angle 90
0 1.4158 1.4226 1.3985 1.4223 118.2742 116.1824 115.5391 269.55055 30 1.4135 1.416 1.4018 1.4209 118.0791 116.8468 116.6304 269.55188 60 1.4151 1.4043 1.4061 1.4185 116.2563 116.6212 117.2755 269.55537 90 1.4179 1.4044 1.4044 1.4179 116.2628 115.1166 116.2796 269.55585 120 1.417 1.4124 1.3979 1.4181 115.6668 112.1427 114.9257 269.55415 150 1.4137 1.415 1.3906 1.4194 114.2752 109.7196 114.1571 269.555 180 1.4121 1.4136 1.3865 1.4208 112.3579 109.231 114.2246 269.55631 Torsion Angle 60
0 1.413 1.4225 1.4002 1.4232 121.4449 119.8148 117.8014 269.54516
30 1.41 1.4171 1.4042 1.4177 122.5364 121.3161 119.7811 269.54431
60 1.4141 1.407 1.4068 1.414 119.521 120.3011 119.7414 269.55021
90 1.4182 1.4055 1.4042 1.415 117.5742 116.6345 116.3454 269.55537 120 1.4174 1.4123 1.3977 1.4185 115.6184 112.5213 113.9391 269.5563 150 1.4136 1.4141 1.3896 1.4212 114.298 110.6075 113.7901 269.5572 180 1.4128 1.4132 1.3854 1.4231 112.3062 110.3493 113.9267 269.55798 Torsion Angle 30
30 1.411 1.4158 1.4157 1.411 124.578 123.8252 124.5735 269.53481
60 1.418 1.4047 1.4175 1.4101 119.5246 121.3414 122.4151 269.5443
90 1.4209 1.4017 1.4162 1.4136 116.6379 116.837 118.014 269.55188
120 1.4176 1.407 1.4091 1.4184 115.4099 113.4605 116.4735 269.55196 150 1.4138 1.4091 1.3995 1.4211 114.2078 111.6546 116.4251 269.55248 180 1.4127 1.4089 1.3949 1.4224 112.3904 111.2702 116.3876 269.55331 Torsion Angle 0
0 1.4097 1.4195 1.4195 1.4095 126.5359 124.7704 126.5985 269.52798 30 1.4143 1.4129 1.4208 1.4103 123.6142 123.5958 125.525 269.53339 60 1.4236 1.4004 1.4231 1.4133 117.6987 119.7624 121.2795 269.54519 90 1.4223 1.3986 1.423 1.4159 115.4582 116.0789 118.1239 269.55052 120 1.4183 1.4047 1.4162 1.4185 115.3538 113.6209 117.5857 269.54884 150 1.4145 1.4076 1.4063 1.4207 113.8942 112.0128 117.9892 269.54887 180 1.413 1.4064 1.4017 1.4213 112.3655 111.5699 118.0331 269.54984 Torsion Angle 30
0 1.4103 1.4208 1.413 1.4143 125.5787 123.6161 123.5116 269.53331
30 1.4193 1.4128 1.413 1.4194 120.6099 120.5849 120.4148 269.542
60 1.4238 1.4002 1.4156 1.4216 115.0575 117.054 117.8701 269.55309
90 1.4224 1.402 1.4135 1.419 114.3219 114.8654 115.5432 269.5559
120 1.4183 1.4079 1.4084 1.4197 115.2646 113.259 115.8224 269.55246 150 1.4143 1.41 1.3993 1.4216 113.6541 111.8039 116.2827 269.55208 180 1.4127 1.409 1.3949 1.4224 112.3805 111.2768 116.3838 269.55331 Torsion Angle 60
0 1.413 1.4225 1.4002 1.4233 121.5099 119.843 117.7736 269.54517
30 1.4212 1.4159 1.4014 1.4274 116.8574 116.557 115.1305 269.55315 60 1.4225 1.404 1.4037 1.4224 113.3995 114.6796 113.5111 269.56204 90 1.4207 1.406 1.4039 1.4205 114.0904 113.5873 113.2119 269.56054 120 1.4165 1.4127 1.3969 1.4206 115.0502 112.2769 113.4656 269.55671 150 1.4129 1.4139 1.3895 1.4223 113.799 110.6815 113.736 269.55659 180 1.4125 1.4129 1.3855 1.4228 112.3241 110.3371 113.9398 269.55792 Torsion Angle 90
0 1.4158 1.4226 1.3984 1.4223 118.2688 116.1824 115.5494 269.55053 30 1.4192 1.4139 1.402 1.4224 115.4079 114.7942 114.3233 269.55592 60 1.4201 1.4034 1.4061 1.4208 113.4455 113.7872 114.0691 269.56058 90 1.4194 1.406 1.4046 1.4189 114.1326 112.9659 114.2777 269.55833
120 1.4157 1.412 1.3986 1.4191 115.0777 111.442 114.471 269.5546
150 1.4121 1.4134 1.3903 1.4205 114.0315 109.7635 114.5542 269.55495
180 1.4121 1.4136 1.3866 1.4208 112.358 109.232 114.224 269.55631
Torsion Angle 120
0 1.4185 1.4163 1.4045 1.4182 117.521 113.5798 115.3203 269.54884
30 1.4197 1.4082 1.408 1.4184 115.8751 113.2805 115.218 269.55244
60 1.4206 1.3969 1.4128 1.4164 113.4502 112.2319 115.0231 269.55679 90 1.4189 1.3985 1.4119 1.4153 114.5389 111.4224 115.1256 269.55468 120 1.4162 1.405 1.4051 1.4163 115.2765 109.7037 115.2128 269.55125 150 1.4133 1.4077 1.3965 1.4173 113.8691 108.0883 115.2917 269.5517 180 1.4121 1.4078 1.393 1.4169 112.2995 107.7269 115.1289 269.55245 Torsion Angle 150
0 1.4207 1.4065 1.4075 1.4143 117.889 111.9462 114.022 269.54882
30 1.4216 1.3996 1.4097 1.4141 116.2088 111.7104 113.8062 269.55206 60 1.4224 1.3894 1.4136 1.4125 113.6504 110.6422 113.8618 269.55658 90 1.4204 1.3902 1.4137 1.4124 114.6798 109.8314 113.8279 269.55495 120 1.4173 1.3965 1.4076 1.4132 115.2972 108.0336 113.9541 269.55178
150 1.414 1.3994 1.3993 1.414 113.9954 106.6015 114.0057 269.5516
0 1.4214 1.4017 1.4068 1.413 118.0759 111.6146 112.3966 269.54982
30 1.4223 1.395 1.4087 1.4126 116.3469 111.222 112.4616 269.55339
60 1.4231 1.3856 1.413 1.4122 113.7748 110.2495 112.5018 269.55793 90 1.4206 1.3864 1.4135 1.4121 114.329 109.2275 112.3704 269.55635 120 1.4168 1.3931 1.4077 1.4123 115.2304 107.8063 112.3215 269.55244 150 1.4134 1.3958 1.3995 1.4126 113.9948 106.3693 112.3146 269.55209 180 1.4126 1.3956 1.3955 1.4126 112.4333 105.9712 112.433 269.55299 Bond lengths are in Å, bond angles are in degreees,and energies are in Hartrees.
*See Figure 1a for atom numberings
Table 7
Experimental and Calculated Atomization Energies
Method Atomization Energy (kcal/mole)
Experimental 1164.97*
MP2 1131.93
DFT 1260.88
