Table S1: The distances between the hydrogen interacting with the cloud and all the atoms members of furan ring in 1-H2O-B at MP2/6-31+G*theoretical level.
Distance / (Å)H10-O1 / 2.880
H10-C2 / 2.910
H10-C3 / 2.980
H10-C4 / 2.990
H10-C5 / 2.930
Table S3: The distances between the hydrogen interacting with the cloud and all the atoms members of thiophene ring in 2-H2O-B at MP2/6-31+G*theoretical level.
Distance / (Å)H10-S1 / 3.140
H10-C2 / 2.600
H10-C3 / 2.480
H10-C4 / 2.800
H10-C5 / 3.120
Table S4: Lone pair occupancies in heterocyclic molecules at B3LYP/6-31+G* level.
Molecule / Occupancy / Molecule / Occupancy / Molecule / Occupancy1 / LP(1)O1 / 1.97 / 2 / LP(1)S1 / 1.98 / 3 / LP(1)Se1 / 1.99
LP(2)O1 / 1.70 / LP(2)S1 / 1.63 / LP(2)Se1 / 1.64
4 / LP(1)O1 / 1.98 / 5 / LP(1)S1 / 1.99 / 6 / LP(1)Se1 / 1.99
LP(2)O1 / 1.69 / LP(2)S1 / 1.60 / LP(2)Se1 / 1.63
LP(1)N2 / 1.96 / LP(1)N2 / 1.94 / LP(1)N2 / 1.95
7 / LP(1)O1 / 1.97 / 8 / LP(1)S1 / 1.98 / 9 / LP(1)Se1 / 1.99
LP(2)O1 / 1.69 / LP(2)S1 / 1.61 / LP(2)Se1 / 1.62
LP(1)N3 / 1.92 / LP(1)N3 / 1.89 / LP(1)N3 / 1.88
Table S5: Lone pair occupancies in adducts of 1-9 with water at B3LYP/6-31+G* level calculated using NBO analysis.
Species / Occupancy / Species / Occupancy / Species / Occupancy1-H2O-A / LP(1)O1 / 1.96 / 2-H2O-A / LP(1)S1 / 1.98 / 3-H2O-A / LP(1)Se1 / 1.99
LP(2)O1 / 1.72 / LP(2)S1 / 1.63 / LP(2)Se1 / 1.65
1-H2O-B / LP(1)O1 / 1.98 / 2-H2O-B / LP(1)S1 / 1.99 / 3-H2O-B / LP(1)Se1 / 1.99
LP(2)O1 / 1.70 / LP(2)S1 / 1.66 / LP(2)Se1 / 1.70
3-H2O-C / LP(1)Se1 / 1.99
LP(2)Se1 / 170
4-H2O-A / LP(1)O1 / 1.97 / 5-H2O-A / LP(1)S1 / 1.99 / 6-H2O-A / LP(1)Se1 / 1.99
LP(2)O1 / 1.69 / LP(2)S1 / 1.61 / LP(2)Se1 / 1.63
LP(1)N2 / 1.94 / LP(1)N2 / 1.94 / LP(1)N2 / 1.95
4-H2O-B / LP(1)O1 / 1.98 / 5-H2O-B / LP(1)S1 / 1.99 / 6-H2O-B / LP(1)Se1 / 1.99
LP(2)O1 / 1.76 / LP(2)S1 / 1.60 / LP(2)Se1 / 1.60
LP(1)N2 / 1.96 / LP(1)N2 / 1.93 / LP(1)N2 / 1.94
7-H2O-A / LP(1)O1 / 1.97 / 8-H2O-A / LP(1)S1 / 1.99 / 9-H2O-A / LP(1)Se1 / 1.99
LP(2)O1 / 1.70 / LP(2)S1 / 1.61 / LP(2)Se1 / 1.62
LP(1)N3 / 1.92 / LP(1)N3 / 1.90 / LP(1)N3 / 1.88
7-H2O-B / LP(1)O1 / 1.97 / 8-H2O-B / LP(1)S1 / 1.98 / 9-H2O-B / LP(1)Se1 / 1.99
LP(2)O1 / 1.68 / LP(2)S1 / 1.60 / LP(2)Se1 / 1.61
LP(1)N3 / 1.90 / LP(1)N3 / 1.88 / LP(1)N3 / 1.87
Table S6: Atomic Charges on different atoms in 1-3 heterocyclic molecules and their adducts with water at B3LYP/6-31+G* level calculated using NBO analysis.
Site / 1 / 1-H2O-A / 1-H2O-B / Site / 2 / 2-H2O-A / 2-H2O-B / Site / 3 / 3-H2O-A / 3-H2O-B / 3-H2O-CO1 / -0.464 / -0.494 / -0.474 / S1 / 0.447 / 0.434 / 0.457 / Se1 / 0.542 / 0.527 / 0.551 / 0.530
C2 / 0.086 / 0.088 / 0.081 / C2 / -0.454 / -0.458 / -0.469 / C2 / -0.498 / -0.502 / -0.493 / -0.493
C3 / -0.340 / -0.331 / -0.342 / C3 / -0.287 / -0.289 / -0.302 / C3 / -0.289 / -0.291 / -0.289 / -0.288
C4 / -0.330 / -0.332 / -0.342 / C4 / -0.287 / -0.293 / -0.287 / C4 / -0.289 / -0.292 / -0.287 / -0.288
C5 / 0.086 / 0.088 / 0.082 / C5 / -0.454 / -0.450 / -0.452 / C5 / -0.498 / -0.491 / -0.530 / -0.492
H6 / 0.232 / 0.239 / 0.239 / H6 / 0.265 / 0.287 / 0.268 / H6 / 0.264 / 0.284 / 0.276 / 0.268
H7 / 0.253 / 0.258 / 0.259 / H7 / 0.252 / 0.250 / 0.257 / H7 / 0.252 / 0.250 / 0.258 / 0.256
H8 / 0.253 / 0.257 / 0.259 / H8 / 0.252 / 0.249 / 0.261 / H8 / 0.252 / 0.249 / 0.255 / 0.256
H9 / 0.232 / 0.238 / 0.239 / H9 / 0.265 / 0.261 / 0.274 / H9 / 0.264 / 0.261 / 0.266 / 0.269
H10 / - / 0.501 / 0.494 / H10 / - / 0.500 / 0.495 / H10 / - / 0.501 / 0.495 / 0.484
O11 / - / -1.000 / -0.992 / O11 / - / -0.994 / -0.991 / O11 / - / -0.996 / -0.992 / -0.991
H12 / - / 0.487 / 0.494 / H12 / - / 0.501 / 0.490 / H12 / - / 0.501 / 0.490 / 0.490
Table S7:Atomic Charges on different atoms in 4-6 heterocyclic molecules and their adducts with water at B3LYP/6-31+G*level calculated using NBO analysis.
Site / 4 / 4-H2O-A / 4-H2O-B / Site / 5 / 5-H2O-A / 5-H2O-B / Site / 6 / 6-H2O-A / 6-H2O-BO1 / -0.322 / -0.348 / -0.313 / S1 / 0.642 / 0.630 / 0.665 / Se1 / 0.719 / 0.718 / 0.769
N2 / -0.138 / -0.142 / -0.176 / N2 / -0.618 / -0.625 / -0.668 / N2 / -0.646 / -0.658 / -0.718
C3 / 0.049 / -0.044 / -0.028 / C3 / -0.013 / -0.014 / 0.006 / C3 / -0.008 / -0.012 / 0.002
C4 / -0.385 / -0.385 / -0.380 / C4 / -0.331 / -0.339 / -0.327 / C4 / -0.337 / -0.347 / -0.330
C5 / 0.136 / 0.145 / 0.143 / C5 / -0.450 / -0.446 / -0.443 / C5 / -0.493 / -0.478 / -0.501
H6 / 0.242 / 0.261 / 0.246 / H6 / 0.270 / 0.291 / 0.273 / H6 / 0.268 / 0.278 / 0.273
H7 / 0.263 / 0.264 / 0.267 / H7 / 0.258 / 0.256 / 0.263 / H7 / 0.257 / 0.254 / 0.262
H8 / 0.253 / 0.253 / 0.262 / H8 / 0.242 / 0.238 / 0.252 / H8 / 0.240 / 0.234 / 0.261
H9 / - / 0.505 / 0.503 / H9 / - / 0.503 / 0.507 / H9 / - / 0.504 / 0.508
O10 / - / -1.007 / -1.010 / O10 / - / -0.997 / -1.011 / O10 / - / -0.997 / -1.014
H11 / - / 0.497 / 0.485 / H11 / - / 0.503 / 0.483 / H11 / - / 0.504 / 0.488
Table S8:Atomic Charges on different atoms in 7-9 heterocyclic molecules and their adducts with water at B3LYP/6-31+G*level calculated using NBO analysis.
Site / 7 / 7-H2O-A / 7-H2O-B / Site / 8 / 8-H2O-A / 8-H2O-B / Site / 9 / 9-H2O-A / 9-H2O-BO1 / -0.468 / -0.493 / -0.459 / S1 / 0.418 / 0.409 / 0.445 / Se1 / 0.503 / 0.508 / 0.534
C2 / 0.327 / 0.326 / 0.343 / C2 / -0.180 / -0.190 / -0.171 / C2 / -0.208 / -0.218 / -0.202
N3 / -0.491 / -0.488 / -0.531 / N3 / -0.457 / -0.459 / -0.501 / N3 / -0.459 / -0.468 / -0.507
C4 / -0.131 / -0.133 / -0.122 / C4 / -0.074 / -0.083 / -0.064 / C4 / -0.080 / -0.084 / -0.075
C5 / 0.048 / 0.056 / 0.060 / C5 / -0.478 / -0.473 / -0.474 / C5 / -0.526 / -0.517 / -0.518
H6 / 0.240 / 0.259 / 0.243 / H6 / 0.271 / 0.292 / 0.274 / H6 / 0.270 / 0.281 / 0.272
H7 / 0.248 / 0.249 / 0.253 / H7 / 0.247 / 0.244 / 0.251 / H7 / 0.248 / 0.244 / 0.251
H8 / 0.228 / 0.227 / 0.238 / H8 / 0.254 / 0.251 / 0.265 / H8 / 0.252 / 0.247 / 0.268
H9 / - / 0.502 / 0.507 / H9 / - / 0.503 / 0.505 / H9 / - / 0.502 / 0.506
O10 / - / -1.001 / -1.014 / O10 / - / -0.997 / -1.014 / O10 / - / -0.997 / -1.016
H11 / - / 0.497 / 0.483 / H11 / - / 0.502 / 0.483 / H11 / - / 0.502 / 0.486
TableS9:Geometrical parameters of heterocyclic molecules1-3 at B3LYP/6-31+G* (L1) and MP2/6-31+G* (L2) theoretical levels.
(Distances are in Å and angles in degrees).
Parameters / 1 / Parameters / 2 / Parameters / 3L1 / L2 / L1 / L2 / L1 / L2
C2-O1 / 1.366 / 1.369 / C2-S1 / 1.736 / 1.717 / C2-Se1 / 1.863 / 1.850
C3-C2 / 1.366 / 1.369 / C3-C2 / 1.370 / 1.380 / C3-C2 / 1.360 / 1.370
C4-C3 / 1.430 / 1.420 / C4-C3 / 1.430 / 1.420 / C4-C3 / 1.430 / 1.420
C5-C4 / 1.360 / 1.360 / C5-C4 / 1.370 / 1.380 / C5-C4 / 1.360 / 1.370
H6-C5 / 1.070 / 1.080 / H6-C5 / 1.080 / 1.080 / H6-C5 / 1.080 / 1.080
H7-C4 / 1.080 / 1.080 / H7-C4 / 1.080 / 1.080 / H7-C4 / 1.080 / 1.080
H8-C3 / 1.080 / 1.080 / H8-C3 / 1.080 / 1.080 / H8-C3 / 1.080 / 1.080
H9-C2 / 1.070 / 1.080 / H9-C2 / 1.080 / 1.080 / H9-C2 / 1.080 / 1.080
C3-C2-O1 / 110.3 / 110.12 / C3-C2-S1 / 115.5 / 111.61 / C3-C2-Se1 / 111.6 / 111.6
C4-C3-C2 / 106.3 / 106.30 / C4-C3-C2 / 112.3 / 112.04 / C4-C3-C2 / 114.0 / 113.9
C5-C4-C3 / 106.3 / 106.67 / C5-C4-C3 / 112.7 / 112.36 / C5-C4-C3 / 114.7 / 114.6
H6-C5-C4 / 134.1 / 134.30 / H6-C5-C4 / 128.3 / 128.10 / H6-C5-C4 / 127.5 / 127.4
H7-C4-C3 / 127.4 / 127.36 / H7-C4-C3 / 124.0 / 124.48 / H7-C4-C3 / 122.7 / 123.2
H8-C3-C2 / 126.3 / 125.94 / H8-C3-C2 / 123.7 / 123.45 / H8-C3-C2 / 123.2 / 122.8
H9-C2-O1 / 115.6 / 115.56 / H9-C2-S1 / 119.9 / 120.04 / H9-C2-Se1 / 120.4 / 120.6
C4-C3-C2-O1 / 0.0 / 0.0 / C4-C3-C2-S1 / -0.0 / 0.0 / C4-C3-C2-Se1 / 0.0 / 0.0
C5-C4-C3-O1 / 0.0 / 0.0 / C5-C4-C3-S1 / 0.0 / 0.0 / C5-C4-C3-Se1 / 0.0 / 0.0
H6-C5-C4-C3 / 180.0 / 180.0 / H6-C5-C4-C3 / -180.0 / 180.0 / H6-C5-C4-C3 / 180.0 / 180.0
H7-C4-C3-C2 / 180.0 / 180.0 / H7-C4-C3-C2 / -180.0 / 179.9 / H7-C4-C3-C2 / 180.0 / 180.0
H8-C3-C2-O1 / 180.0 / 180.0 / H8-C3-C2-S1 / 180.0 / -180.0 / H8-C3-C2-Se1 / 180.0 / 180.0
H9-C2-O1-C5 / 180.0 / 180.0 / H9-C2-S1-C5 / -180.0 / 180.0 / H9-C2-Se1-C5 / 180.0 / 180.0
Table S10: Geometrical parameters of heterocyclic molecules4-6 at B3LYP/6-31+G* (L1) and MP2/6-31+G* (L2) theoretical levels.
(Distances are in Å and angles in degrees)
Parameters / 4 / Parameters / 5 / Parameters / 6L1 / L2 / L1 / L2 / L1 / L2
N2-O1 / 1.400 / 1.395 / N2-S1 / 1.681 / 1.666 / N2-Se1 / 1.800 / 1.811
C3-N2 / 1.310 / 1.330 / C3-N2 / 1.310 / 1.340 / C3-N2 / 1.300 / 1.330
C4-C3 / 1.420 / 1.410 / C4-C3 / 1.420 / 1.410 / C4-C3 / 1.430 / 1.410
C5-C4 / 1.360 / 1.360 / C5-C4 / 1.370 / 1.383 / C5-C4 / 1.360 / 1.380
H6-C5 / 1.080 / 1.080 / H6-C5 / 1.080 / 1.080 / H6-C5 / 1.080 / 1.080
H7-C4 / 1.070 / 1.080 / H7-C4 / 1.080 / 1.080 / H7-C4 / 1.080 / 1.080
H8-C3 / 1.080 / 1.080 / H8-C3 / 1.080 / 1.080 / H8-C3 / 1.080 / 1.080
C3-N2-O1 / 105.1 / 105.01 / C3-N2-S1 / 108.6 / 108.29 / C3-N2-Se1 / 109.7 / 107.9
C4-C3-N2 / 112.5 / 112.20 / C4-C3-N2 / 117.1 / 116.65 / C4-C3-N2 / 118.0 / 119.0
C5-C4-C3 / 103.1 / 103.82 / C5-C4-C3 / 110.1 / 110.11 / C5-C4-C3 / 112.5 / 112.7
H6-C5-C4 / 134.0 / 134.75 / H6-C5-C4 / 128.6 / 128.44 / H6-C5-C4 / 127.4 / 127.5
H7-C4-C3 / 128.6 / 128.47 / H7-C4-C3 / 124.9 / 125.23 / H7-C4-C3 / 123.4 / 123.7
H8-C3-C4 / 128.8 / 129.56 / H8-C3-C4 / 124.7 / 125.76 / H8-C3-C4 / 123.1 / 123.9
C4-C3-N2-O1 / 0.1 / 0.0 / C4-C3-N2-S1 / 0.0 / 0.0 / C4-C3-N2-Se1 / 0.0 / 0.0
C5-C4-C3-O1 / -0.0 / -0.0 / C5-C4-C3-S1 / 0.0 / 0.0 / C5-C4-C3-Se1 / 0.0 / 0.0
H6-C5-C4-C3 / 179.8 / 179.9 / H6-C5-C4-C3 / -180.0 / -180.0 / H6-C5-C4-C3 / 180.0 / 180.0
H7-C4-C3-N2 / 180.0 / -180.0 / H7-C4-C3-N2 / -180.0 / -180.0 / H7-C4-C3-N2 / 180.0 / 180.0
H8-C3-C4-C5 / -180.0 / 180.0 / H8-C3-C4-C5 / 180.0 / -180.0 / H8-C3-C4-C5 / 180.0 / 180.0
Table S11: Geometrical parameters of heterocyclic molecules7-9 at B3LYP/6-31+G* (L1) and MP2/6-31+G* (L2) theoretical levels.(Distances are in Å and angles in degrees)
Parameters / 7 / Parameters / 8 / Parameters / 9L1 / L2 / L1 / L2 / L1 / L2
C2-O1 / 1.350 / 1.364 / C2-S1 / 1.748 / 1.726 / C2-Se1 / 1.885 / 1.867
N3-C2 / 1.280 / 1.300 / N3-C2 / 1.300 / 1.310 / N3-C2 / 1.290 / 1.310
C4-N3 / 1.390 / 1.390 / C4-N3 / 1.370 / 1.370 / C4-N3 / 1.380 / 1.370
C5-C4 / 1.350 / 1.360 / C5-C4 / 1.360 / 1.370 / C5-C4 / 1.360 / 1.370
H6-C5 / 1.070 / 1.080 / H6-C5 / 1.080 / 1.080 / H6-C5 / 1.082 / 1.085
H7-C4 / 1.080 / 1.080 / H7-C4 / 1.080 / 1.080 / H7-C4 / 1.082 / 1.085
H8-C2 / 1.080 / 1.080 / H8-C2 / 1.080 / 1.080 / H8-C2 / 1.082 / 1.085
N3-C2-O1 / 114.7 / 114.69 / N3-C2-S1 / 115.0 / 115.32 / N3-C2-Se1 / 115.0 / 114.9
C4-N3-C2 / 104.4 / 104.04 / C4-N3-C2 / 109.8 / 110.13 / C4-N3-C2 / 111.4 / 111.2
C5-C4-N3 / 109.1 / 109.35 / C5-C4-N3 / 116.2 / 115.56 / C5-C4-N3 / 117.7 / 117.3
H6-C5-C4 / 135.7 / 135.58 / H6-C5-C4 / 128.8 / 128.47 / H6-C5-C4 / 127.3 / 127.3
H7-C4-N3 / 121.8 / 121.73 / H7-C4-N3 / 118.9 / 119.52 / H7-C4-N3 / 118.1 / 119.4
H8-C2-O1 / 116.5 / 116.58 / H8-C2-S1 / 120.3 / 120.90 / H8-C2-S1 / 120.8 / 121.1
C4-N3-C2-O1 / 0.0 / 0.0 / C4-N3-C2-S1 / 0.0 / -0.0 / C4-N3-C2-Se1 / 0.0 / -0.0
C5-C4-N3-O1 / 0.0 / 0.0 / C5-C4-N3-S1 / 0.0 / 0.0 / C5-C4-N3-Se1 / 0.0 / -0.0
H6-C5-C4-N3 / 180.0 / 180.0 / H6-C5-C4-N3 / 180.0 / 180.0 / H6-C5-C4-N3 / 180.0 / -180.0
H7-C4-N3-C2 / 180.0 / 180.0 / H7-C4-N3-C2 / 180.0 / -180.0 / H7-C4-N3-C2 / 180.0 / -180.0
H8-C2-O1-C5 / 180.0 / 180.0 / H8-C2-S1-C5 / -180.0 / 180.0 / H8-C2-Se1-C5 / 180.0 / -180.0
Table S12:Geometrical parameters of 1-H2O-A, 2-H2O-A and 3-H2O-Aadducts at B3LYP/6-31+G* (L1) and MP2/6-31+G* (L2) theoretical levels. (Distances are in Å and angles in degrees)
Parameters / 1-H2O-A / Parameters / 2-H2O-A / Parameters / 3-H2O-AL1 / L2 / L1 / L2 / L1 / L2
C2-O1 / 1.370 / 1.373 / C2-S1 / 1.736 / 1.718 / C2-Se1 / 1.867 / 1.854
C3-C2 / 1.360 / 1.366 / C3-C2 / 1.371 / 1.380 / C3-C2 / 1.367 / 1.377
C4-C3 / 1.438 / 1.431 / C4-C3 / 1.431 / 1.421 / C4-C3 / 1.430 / 1.422
C5-C4 / 1.360 / 1.366 / C5-C4 / 1.371 / 1.380 / C5-C4 / 1.360 / 1.378
H6-C5 / 1.079 / 1.080 / H6-C5 / 1.084 / 1.084 / H6-C5 / 1.083 / 1.084
H7-C4 / 1.081 / 1.082 / H7-C4 / 1.085 / 1.086 / H7-C4 / 1.086 / 1.086
H8-C3 / 1.081 / 1.082 / H8-C3 / 1.085 / 1.086 / H8-C3 / 1.086 / 1.087
H9-C2 / 1.079 / 1.080 / H9-C2 / 1.082 / 1.083 / H9-C2 / 1.082 / 1.087
H10-O1 / 2.02 / 2.00 / H10-S1 / 4.829 / 4.940 / H10-Se1 / 5.514 / 5.431
O11-H10 / 0.973 / 0.974 / O11-H10 / 0.969 / 0.972 / O11-H10 / 0.970 / 0.972
H12-O11 / 0.968 / 0.970 / H12-O11 / 0.969 / 0.972 / H12-O11 / 0.970 / 0.972
C3-C2-O1 / 110.07 / 110.02 / C3-C2-S1 / 111.38 / 111.48 / C3-C2-Se1 / 111.3 / 111.0
C4-C3-C2 / 106.37 / 106.50 / C4-C3-C2 / 112.67 / 112.30 / C4-C3-C2 / 114.7 / 114.7
C5-C4-C3 / 106.37 / 106.51 / C5-C4-C3 / 112.95 / 112.69 / C5-C4-C3 / 115.0 / 115.0
H6-C5-C4 / 134.29 / 134.44 / H6-C5-C4 / 129.10 / 128.82 / H6-C5-C4 / 126.7 / 126.5
H7-C4-C3 / 127.27 / 127.45 / H7-C4-C3 / 123.92 / 124.42 / H7-C4-C3 / 122.8 / 123.2
H8-C3-C2 / 126.35 / 126.04 / H8-C3-C2 / 123.33 / 123.15 / H8-C3-C2 / 122.5 / 122.2
H9-C2-O1 / 115.62 / 115.57 / H9-C2-S1 / 120.95 / 120.44 / H9-C2-Se1 / 121.1 / 121.3
H10-X1-C5 / 125.08 / 125.08 / H10-S1-C5 / 51.92 / 46.62 / H10-Se1-C5 / 28.5 / 28.2
O11-H10-O1 / 177.07 / 179.19 / O11-H10-S1 / 54.95 / 47.81 / O11-H10-Se1 / 47.1 / 47.1
H12-O11-H10 / 105.43 / 105.33 / H12-O11-H10 / 105.56 / 105.40 / H12-O11-H10 / 105.6 / 105.4
C4-C3-C2-O1 / 0.1 / 0.1 / C4-C3-C2-S1 / -0.0 / 0.0 / C4-C3-C2-Se1 / 0.0 / 0.0
C5-C4-C3-O1 / 0.0 / 0.0 / C5-C4-C3-S1 / 0.0 / -0.0 / C5-C4-C3-Se1 / 0.0 / 0.1
H6-C5-C4-C3 / 179.6 / 179.5 / H6-C5-C4-C3 / 179.0 / 180.0 / H6-C5-C4-C3 / -179.9 / -180.0
H7-C4-C3-C2 / 179.9 / 179.9 / H7-C4-C3-C2 / 180.0 / 180.0 / H7-C4-C3-C2 / -179.9 / -180.0
H8-C3-C2-O1 / 179.9 / 179.9 / H8-C3-C2-S1 / 180.0 / 180.0 / H8-C3-C2-Se1 / -179.9 / -180.0
H9-C2-O1-C5 / 179.6 / 179.6 / H9-C2-S1-C5 / 180.0 / -180.0 / H9-C2-Se1-C5 / 180.0 / 180.0
H10-X1-C5-C4 / 179.0 / 176.3 / H10-S1-C5-C4 / 169.5 / 167.3 / H10-Se1-C5-C4 / 161.5 / 160.1
O11-H10-O1-C2 / 244.5 / 239.7 / O11-H10-S1-C2 / 67.5 / 81.6 / O11-H10-Se1-C2 / 90.0 / 98.1
H12-O11-H10-O1 / 26.7 / 30.3 / H12-O11-H10-S1 / 124.9 / 148.1 / H12-O11-H10-Se1 / 168.3 / 169.33
Table S13:Geometrical parameters of 4-H2O-A, 5-H2O-A and 6-H2O-Aadducts at B3LYP/6-31+G* (L1) and MP2/6-31+G* (L2) theoretical levels. (Distances are in Å and angles in degrees)
Parameters / 4-H2O-A / Parameters / 5-H2O-A / Parameters / 6-H2O-AL1 / L2 / L1 / L2 / L1 / L2
N2-O1 / 1.404 / 1.397 / N2-S1 / 1.684 / 1.668 / N2-Se1 / 1.826 / 1.814
C3-N2 / 1.312 / 1.329 / C3-N2 / 1.320 / 1.341 / C3-N2 / 1.313 / 1.337
C4-C3 / 1.426 / 1.417 / C4-C3 / 1.427 / 1.414 / C4-C3 / 1.434 / 1.420
C5-C4 / 1.361 / 1.365 / C5-C4 / 1.373 / 1.383 / C5-C4 / 1.367 / 1.379
H6-C5 / 1.081 / 1.081 / H6-C5 / 1.085 / 1.085 / H6-C5 / 1.081 / 1.083
H7-C4 / 1.080 / 1.080 / H7-C4 / 1.084 / 1.085 / H7-C4 / 1.085 / 1.086
H8-C3 / 1.083 / 1.083 / H8-C3 / 1.087 / 1.086 / H8-C3 / 1.089 / 1.088
H9-O1 / 2.170 / 2.211 / H9-S1 / 4.943 / 4.928 / H9-Se1 / 3.557 / 3.562
O10-H9 / 0.972 / 0.974 / O10-H9 / 0.969 / 0.972 / O10-H9 / 0.970 / 0.973
H11-O10 / 0.968 / 0.971 / H11-O10 / 0.969 / 0.972 / H11-O10 / 0.970 / 0.973
C3-N2-O1 / 104.84 / 104.90 / C3-N2-S1 / 108.39 / 108.10 / C3-N2-Se1 / 108.53 / 108.04
C4-C3-N2 / 112.56 / 112.25 / C4-C3-N2 / 117.27 / 116.80 / C4-C3-N2 / 119.41 / 119.13
C5-C4-C3 / 103.34 / 103.92 / C5-C4-C3 / 110.39 / 110.44 / C5-C4-C3 / 112.33 / 112.57
H6-C5-C4 / 134.88 / 135.83 / H6-C5-C4 / 129.12 / 129.33 / H6-C5-C4 / 128.45 / 128.61
H7-C4-C3 / 128.44 / 128.43 / H7-C4-C3 / 124.74 / 125.07 / H7-C4-C3 / 123.39 / 123.63
H8-C3-C4 / 128.80 / 129.43 / H8-C3-C4 / 124.82 / 125.81 / H8-C3-C4 / 123.08 / 124.01
H9-O1-C5 / 104.22 / 103.33 / H9-S1-C5 / 46.17 / 45.90 / H9-Se1-C5 / 82.55 / 80.05
O10-H9-O1 / 128.44 / 122.55 / O10-H9-S1 / 50.83 / 47.47 / O10-H9-Se1 / 54.57 / 51.76
H11-O10-H9 / 106.17 / 105.89 / H11-O10-H9 / 105.61 / 105.38 / H11-O10-H9 / 105.45 / 105.31
C4-C3-N2-O1 / -0.0 / -0.0 / C4-C3-N2-S1 / -0.0 / -0.0 / C4-C3-N2-Se1 / 0.0 / -0.0
C5-C4-C3-O1 / -0.0 / -0.0 / C5-C4-C3-S1 / -0.0 / -0.0 / C5-C4-C3-Se1 / 0.0 / 0.0
H6-C5-C4-C3 / 180.0 / 180.1 / H6-C5-C4-C3 / 180.0 / 180.0 / H6-C5-C4-C3 / 180.0 / 180.0
H7-C4-C3-N2 / 180.0 / 180.1 / H7-C4-C3-N2 / 180.0 / 180.0 / H7-C4-C3-N2 / 180.0 / 180.0
H8-C3-C4-C5 / 180.0 / 180.0 / H8-C3-C4-C5 / 180.0 / 180.0 / H8-C3-C4-C5 / 180.0 / 180.0
H9-O1-C5-C4 / 180.0 / 183.2 / H9-S1-C5-C4 / 193.6 / 192.2 / H9-Se1-C5-C4 / 167.1 / 166.7
O10-H9-O1-N2 / 180.1 / 184.5 / O10-H9-S1-N2 / 279.7 / 278.6 / O10-H9-Se1-N2 / 117.0 / 115.2
H11-O10-H9-O1 / 180.1 / 194.3 / H11-O10-H9-S1 / 216.6 / 211.3 / H11-O10-H9-Se1 / 120.0 / 126.4
Table S14: Geometrical parameters of 7-H2O-A, 8-H2O-A and 9-H2O-A adducts at B3LYP/6-31+G* (L1) and MP2/6-31+G* (L2) theoretical levels. (Distances are in Å and angles in degrees)
Parameters / 7-H2O-A / Parameters / 8-H2O-A / Parameters / 9-H2O-AL1 / L2 / L1 / L2 / L1 / L2
C2-O1 / 1.362 / 1.366 / C2-S1 / 1.748 / 1.725 / C2-Se1 / 1.885 / 1.867
N3-C2 / 1.293 / 1.304 / N3-C2 / 1.302 / 1.320 / N3-C2 / 1.299 / 1.318
C4-N3 / 1.394 / 1.393 / C4-N3 / 1.380 / 1.375 / C4-N3 / 1.382 / 1.377
C5-C4 / 1.356 / 1.362 / C5-C4 / 1.368 / 1.378 / C5-C4 / 1.364 / 1.375
H6-C5 / 1.079 / 1.079 / H6-C5 / 1.083 / 1.084 / H6-C5 / 1.080 / 1.081
H7-C4 / 1.080 / 1.080 / H7-C4 / 1.084 / 1.084 / H7-C4 / 1.085 / 1.086
H8-C2 / 1.080 / 1.080 / H8-C2 / 1.084 / 1.084 / H8-C2 / 1.085 / 1.085
H9-O1 / 2.220 / 2.252 / H9-S1 / 4.958 / 4.988 / H9-Se1 / 3.684 / 3.704
O10-H9 / 0.971 / 0.973 / O10-H9 / 0.969 / 0.972 / O10-H9 / 0.970 / 0.972
H11-O10 / 0.968 / 0.971 / H11-O10 / 0.969 / 0.972 / H11-O10 / 0.970 / 0.972
N3-C2-O1 / 114.37 / 114.51 / N3-C2-S1 / 115.06 / 115.22 / N3-C2-Se1 / 115.10 / 115.13
C4-N3-C2 / 104.35 / 104.01 / C4-N3-C2 / 110.43 / 109.65 / C4-N3-C2 / 112.27 / 111.66
C5-C4-N3 / 109.42 / 109.67 / C5-C4-N3 / 116.22 / 116.0 / C5-C4-N3 / 117.91 / 117.91
H6-C5-C4 / 136.56 / 136.65 / H6-C5-C4 / 129.38 / 129.10 / H6-C5-C4 / 128.65 / 128.66
H7-C4-N3 / 121.57 / 121.55 / H7-C4-N3 / 118.92 / 119.17 / H7-C4-N3 / 117.91 / 118.08
H8-C2-O1 / 116.86 / 116.78 / H8-C2-S1 / 120.91 / 121.22 / H8-C2-Se1 / 121.82 / 122.12
H9-O1-C5 / 100.94 / 100.02 / H9-S1-C5 / 46.81 / 43.88 / H9-Se1-C5 / 80.37 / 77.09
O10-H9-O1 / 130.09 / 124.46 / O10-H9-S1 / 48.05 / 45.73 / O10-H9-Se1 / 53.30 / 51.19
H11-O10-H9 / 106.24 / 106.00 / H11-O10-H9 / 105.62 / 105.39 / H11-O10-H9 / 105.46 / 105.29
C4-N3-C2-O1 / 0.0 / 0.0 / C4-N3-C2-S1 / 0.0 / 0.0 / C4-N3-C2-Se1 / 0.0 / 0.0
C5-C4-N3-O1 / 0.0 / -0.0 / C5-C4-N3-S1 / -0.0 / 0.0 / C5-C4-N3-Se1 / 0.0 / 0.0
H6-C5-C4-N3 / 180.0 / 180.2 / H6-C5-C4-N3 / 180.0 / 180.0 / H6-C5-C4-N3 / 180.0 / 180.0
H7-C4-N3-C2 / 180.0 / 180.0 / H7-C4-N3-C2 / 180.0 / 180.0 / H7-C4-N3-C2 / 180.0 / 180.0
H8-C2-O1-C5 / 180.0 / 180.0 / H8-C2-S1-C5 / 180.0 / 180.0 / H8-C2-Se1-C5 / 180.0 / 180.0
H9-O1-C5-C4 / 179.5 / 179.6 / H9-S1-C5-C4 / 192.4 / 193.2 / H9-Se1-C5-C4 / 192.3 / 192.4
O10-H9-O1-C2 / 179.1 / 179.1 / O10-H9-S1-C2 / 280.1 / 274.4 / O10-H9-Se1-C2 / 264.0 / 265.7
H11-O10-H9-O1 / 179.6 / 176.9 / H11-O10-H9-S1 / 208.4 / 200.5 / H11-O10-H9-Se1 / 236.6 / 229.8
Table S15: Geometrical parameters of 1-H2O-B, 2-H2O-B and 3-H2O-Badducts at B3LYP/6-31+G* (L1) and MP2/6-31+G* (L2) theoretical levels. (Distances are in Å and angles in degrees)
Parameters / 1-H2O-B / Parameters / 2-H2O-B / Parameters / 3-H2O-BL1 / L2 / L1 / L2 / L1 / L2
C2-O1 / 1.366 / 1.371 / C2-S1 / 1.736 / 1.716 / C2-Se1 / 1.864 / 1.852
C3-C2 / 1.362 / 1.368 / C3-C2 / 1.373 / 1.382 / C3-C2 / 1.367 / 1.378
D4-C3 / 0.719 / 0.715 / D4-C3 / 0.715 / 0.711 / D4-C3 / 0.717 / 0.712
D5-D4 / 1.060 / 1.060 / D5-D4 / 1.275 / 1.275 / D5-D4 / 1.285 / 1.285
C6-D4 / 0.719 / 0.715 / C6-D4 / 0.715 / 0.711 / C6-D4 / 0.717 / 0.712
C7-C6 / 1.365 / 1.368 / C7-C6 / 1.370 / 1.381 / C7-C6 / 1.369 / 1.380
H8-C7 / 1.079 / 1.080 / H8-C7 / 1.082 / 1.083 / H8-C7 / 1.082 / 1.084
H9-C6 / 1.082 / 1.082 / H9-C6 / 1.084 / 1.086 / H9-C6 / 1.086 / 1.087
H10-C3 / 1.081 / 1.082 / H10-C3 / 1.085 / 1.086 / H10-C3 / 1.086 / 1.087
H11-C2 / 1.079 / 1.080 / H11-C2 / 1.082 / 1.084 / H11-C2 / 1.082 / 1.084
H12-D5 / 2.831 / 2.670 / H12-D5 / 2.892 / 2.598 / H12-D5 / 3.028 / 2.928
D13-H12 / 1.000 / 1.000 / D13-H12 / 1.000 / 1.000 / D13-H12 / 1.000 / 1.000
O14-H12 / 0.972 / 0.973 / O14-H12 / 0.972 / 0.974 / O14-H12 / 0.972 / 0.974
H15-O14 / 0.969 / 0.972 / H15-O14 / 0.969 / 0.971 / H15-O14 / 0.969 / 0.971
C3-C2-O1 / 110.40 / 110.20 / C3-C2-S1 / 111.56 / 111.73 / C3-C2-Se1 / 111.70 / 111.59
D4-C3-C2 / 106.30 / 106.30 / D4-C3-C2 / 112.30 / 112.29 / D4-C3-C2 / 114.00 / 114.68
D5-D4-C3 / 90.00 / 90.00 / D5-D4-C3 / 90.00 / 90.00 / D5-D4-C3 / 90.00 / 90.00
C6-D4-D5 / 89.63 / 90.14 / C6-D4-D5 / 90.69 / 89.94 / C6-D4-D5 / 91.12 / 90.81
C7-C6-C3 / 106.14 / 106.37 / C7-C6-C3 / 112.62 / 112.29 / C7-C6-C3 / 114.86 / 114.69
H8-C7-C6 / 133.85 / 134.17 / H8-C7-C6 / 128.24 / 128.00 / H8-C7-C6 / 127.59 / 127.44
H9-C6-C3 / 127.38 / 127.54 / H9-C6-C3 / 123.94 / 124.46 / H9-C6-C3 / 122.70 / 123.20
H10-C3-C2 / 126.57 / 126.08 / H10-C3-C2 / 123.34 / 123.17 / H10-C3-C2 / 122.74 / 122.40
H11-C2-O1 / 115.66 / 115.61 / H11-C2-S1 / 120.16 / 120.27 / H11-C2-Se1 / 120.93 / 121.11
H12-D5-D4 / 73.93 / 90.53 / H12-D5-D4 / 73.97 / 73.85 / H12-D5-D4 / 84.85 / 82.81
D13-H12-D5 / 90.00 / 90.00 / D13-H12-D5 / 90.00 / 90.00 / D13-H12-D5 / 90.00 / 90.00
O14-H12-D13 / 80.80 / 30.74 / O14-H12-D13 / 79.62 / 74.25 / O14-H12-D13 / 74.19 / 73.78
H15-O14-H12 / 105.29 / 103.66 / H15-O14-H12 / 105.17 / 104.70 / H15-O14-H12 / 105.33 / 105.37
D4-C3-C2-O1 / 0.0 / 0.0 / D4-C3-C2-S1 / 0.0 / 0.0 / D4-C3-C2-Se1 / 0.0 / 0.0
D5-D4-C3-C2 / 0.0 / 0.0 / D5-D4-C3-C2 / 0.0 / 0.0 / D5-D4-C3-C2 / 0.0 / 0.0
C6-D4-D5-C3 / 180.1 / 180.7 / C6-D4-D5-C3 / 179.6 / 179.3 / C6-D4-D5-C3 / 180.1 / 180.0
C7-C6-C3-C2 / 0.0 / -0.0 / C7-C6-C3-C2 / -0.0 / -0.1 / C7-C6-C3-C2 / -0.2 / -0.2
H8-C7-C6-C3 / 179.6 / 180.4 / H8-C7-C6-C3 / -179.9 / -180.3 / H8-C7-C6-C3 / 178.7 / 179.3
H9-C6-C3-C2 / 179.1 / 179.6 / H9-C6-C3-C2 / -179.7 / -179.9 / H9-C6-C3-C2 / 179.6 / 179.7
H10-C3-C2-O1 / 180.0 / 179.9 / H10-C3-C2-S1 / 179.4 / 179.5 / H10-C3-C2-Se1 / 180.2 / 179.9
H11-C2-O1-C7 / 179.8 / 179.9 / H11-C2-S1-C7 / -180.7 / -179.6 / H11-C2-Se1-C7 / 180.3 / 180.2
H12-D5-D4-C6 / 63.5 / 90.7 / H12-D5-D4-C6 / 118.7 / 103.0 / H12-D5-D4-C6 / 51.3 / 53.1
D13-H12-D5-D4 / 180.0 / 180.0 / D13-H12-D5-D4 / 180.0 / 180.0 / D13-H12-D5-D4 / 180.0 / 180.0
O14-H12-D13-D5 / -190.8 / -178.0 / O14-H12-D13-D5 / -164.5 / -158.3 / O14-H12-D13-D5 / -180.7 / -179.0
H15-O14-H12-D5 / -15.5 / -0.8 / H15-O14-H12-D5 / 4.9 / 29.0 / H15-O14-H12-D5 / 298.5 / 286.6
D=dummy
Table S16: Geometrical parameters of 4-H2O-B, 5-H2O-B and 6-H2O-Badducts at B3LYP/6-31+G* (L1) and MP2/6-31+G* (L2) theoretical levels.(Distances are in Å and angles in degrees)
Parameters / 4-H2O-B / Parameters / 5-H2O-B / Parameters / 6-H2O-BL1 / L2 / L1 / L2 / L1 / L2
N2-O1 / 1.396 / 1.390 / N2-S1 / 1.681 / 1.665 / N2-Se1 / 1.816 / 1.805
C3-N2 / 1.313 / 1.329 / C3-N2 / 1.321 / 1.342 / C3-N2 / 1.317 / 1.339
C4-C3 / 1.424 / 1.415 / C4-C3 / 1.424 / 1.412 / C4-C3 / 1.430 / 1.416
C5-C4 / 1.362 / 1.366 / C5-C4 / 1.373 / 1.383 / C5-C4 / 1.368 / 1.380
H6-C5 / 1.081 / 1.081 / H6-C5 / 1.083 / 1.084 / H6-C5 / 1.083 / 1.084
H7-C4 / 1.080 / 1.080 / H7-C4 / 1.084 / 1.084 / H7-C4 / 1.085 / 1.086
H8-C3 / 1.083 / 1.083 / H8-C3 / 1.086 / 1.086 / H8-C3 / 1.088 / 1.088
H9-N2 / 2.027 / 2.053 / H9-N2 / 1.994 / 1.995 / H9-N2 / 1.963 / 1.980
O10-H9 / 0.977 / 0.978 / O10-H9 / 0.979 / 0.980 / O10-H9 / 0.979 / 0.980
H11-O10 / 0.968 / 0.970 / H11-O10 / 0.968 / 0.970 / H11-O10 / 0.968 / 0.970
C3-N2-O1 / 105.74 / 105.76 / C3-N2-S1 / 109.18 / 108.92 / C3-N2-Se1 / 108.90 / 108.50
C4-C3-N2 / 111.97 / 111.72 / C4-C3-N2 / 116.75 / 116.29 / C4-C3-N2 / 118.96 / 118.61
C5-C4-C3 / 103.18 / 103.73 / C5-C4-C3 / 110.19 / 110.22 / C5-C4-C3 / 112.68 / 112.97
H6-C5-C4 / 133.89 / 134.69 / H6-C5-C4 / 128.44 / 128.47 / H6-C5-C4 / 127.46 / 127.58
H7-C4-C3 / 128.46 / 128.48 / H7-C4-C3 / 124.76 / 125.11 / H7-C4-C3 / 123.15 / 123.42
H8-C3-C4 / 129.25 / 129.88 / H8-C3-C4 / 125.28 / 126.18 / H8-C3-C4 / 123.79 / 124.80
H9-N2-O1 / 129.39 / 130.89 / H9-N2-S1 / 131.02 / 129.60 / H9-N2-Se1 / 149.36 / 150.51
O10-H9-N2 / 167.08 / 165.11 / O10-H9-N2 / 170.25 / 171.50 / O10-H9-N2 / 151.91 / 150.70
H11-O10-H9 / 105.46 / 105.28 / H11-O10-H9 / 105.52 / 105.26 / H11-O10-H9 / 106.01 / 105.82
C4-C3-N2-O1 / -0.0 / -0.1 / C4-C3-N2-S1 / -0.1 / -0.38 / C4-C3-N2-Se1 / -0.0 / -0.0
C5-C4-C3-O1 / 0.0 / 0.0 / C5-C4-C3-S1 / -0.0 / 0.03 / C5-C4-C3-Se1 / 0.0 / 0.0
H6-C5-C4-C3 / 180.0 / 180.0 / H6-C5-C4-C3 / 179.9 / 180.0 / H6-C5-C4-C3 / 180.0 / 180.0
H7-C4-C3-N2 / 180.0 / 179.9 / H7-C4-C3-N2 / 179.9 / 180.0 / H7-C4-C3-N2 / 180.0 / 180.1
H8-C3-C4-C5 / 180.1 / 180.2 / H8-C3-C4-C5 / 180.3 / 180.6 / H8-C3-C4-C5 / 180.0 / 180.1
H9-N2-O1-C5 / 174.8 / 166.6 / H9-N2-S1-C5 / 171.3 / 154.5 / H9-N2-Se1-C5 / 180.0 / 182.7
O10-H9-N2-O1 / 180.8 / 186.8 / O10-H9-N2-S1 / 196.7 / 210.6 / O10-H9-N2-Se1 / 179.4 / 178.4
H11-O10-H9-O1 / 225.6 / 233.2 / H11-O10-H9-S1 / 234.3 / 237.41 / H11-O10-H9-Se1 / 172.9 / 148.6
Table S17: Geometrical parameters of 7-H2O-B, 8-H2O-B and 9-H2O-Badducts at B3LYP/6-31+G* (L1) and MP2/6-31+G* (L2) theoretical levels. (Distances are in Å and angles in degrees)
Parameters / 7-H2O-B / Parameters / 8-H2O-B / Parameters / 9-H2O-BL1 / L2 / L1 / L2 / L1 / L2
C2-O1 / 1.353 / 1.359 / C2-S1 / 1.740 / 1.719 / C2-Se1 / 1.872 / 1.857
N3-C2 / 1.297 / 1.307 / N3-C2 / 1.305 / 1.322 / N3-C2 / 1.300 / 1.318
C4-N3 / 1.393 / 1.391 / C4-N3 / 1.378 / 1.374 / C4-N3 / 1.380 / 1.374
C5-C4 / 1.356 / 1.363 / C5-C4 / 1.367 / 1.377 / C5-C4 / 1.364 / 1.375
H6-C5 / 1.078 / 1.079 / H6-C5 / 1.081 / 1.083 / H6-C5 / 1.081 / 1.083
H7-C4 / 1.080 / 1.080 / H7-C4 / 1.084 / 1.084 / H7-C4 / 1.085 / 1.085
H8-C2 / 1.080 / 1.080 / H8-C2 / 1.084 / 1.084 / H8-C2 / 1.084 / 1.085
H9-N3 / 1.993 / 2.010 / H9-N3 / 1.985 / 1.993 / H9-N3 / 1.996 / 2.021
O10-H9 / 0.980 / 0.980 / O10-H9 / 0.980 / 0.982 / O10-H9 / 0.980 / 0.981
H11-O10 / 0.968 / 0.970 / H11-O10 / 0.968 / 0.970 / H11-O10 / 0.968 / 0.970
N3-C2-O1 / 114.11 / 114.18 / N3-C2-S1 / 114.86 / 114.95 / N3-C2-Se1 / 114.69 / 114.62
C4-N3-C2 / 104.65 / 104.44 / C4-N3-C2 / 110.91 / 110.27 / C4-N3-C2 / 112.99 / 112.52
C5-C4-N3 / 108.80 / 108.95 / C5-C4-N3 / 115.50 / 115.23 / C5-C4-N3 / 117.48 / 117.40
H6-C5-C4 / 135.56 / 135.48 / H6-C5-C4 / 128.59 / 128.31 / H6-C5-C4 / 127.43 / 127.23
H7-C4-N3 / 121.78 / 121.83 / H7-C4-N3 / 119.16 / 119.46 / H7-C4-N3 / 118.13 / 118.39
H8-C2-O1 / 117.43 / 117.26 / H8-C2-X1 / 121.46 / 121.68 / H8-C2-Se1 / 122.44 / 122.76
H9-N3-C2 / 119.14 / 118.93 / H9-N3-C2 / 114.08 / 113.20 / H9-N3-C2 / 102.36 / 99.23
O10-H9-N3 / 171.48 / 172.82 / O10-H9-N3 / 169.44 / 169.86 / O10-H9-N3 / 155.87 / 152.25
H11-O10-H9 / 105.51 / 105.40 / H11-O10-H9 / 105.59 / 105.33 / H11-O10-H9 / 105.90 / 105.83
C4-N3-C2-O1 / -0.1 / -0.2 / C4-N3-C2-S1 / -0.1 / -0.1 / C4-N3-C2-Se1 / 0.1 / 0.1
C5-C4-N3-O1 / 0.0 / 0.1 / C5-C4-N3-S1 / 0.0 / 0.1 / C5-C4-N3-Se1 / -0.0 / -0.0
H6-C5-C4-N3 / 180.0 / 180.1 / H6-C5-C4-N3 / 180.0 / 180.1 / H6-C5-C4-N3 / 180.0 / 180.0
H7-C4-N3-C2 / 180.3 / 180.2 / H7-C4-N3-C2 / 180.2 / 180.2 / H7-C4-N3-C2 / 179.8 / 179.8
H8-C2-O1-C5 / 180.2 / 180.3 / H8-C2-S1-C5 / 180.3 / 180.4 / H8-C2-Se1-C5 / 179.9 / 179.9
H9-N3-C2-O1 / 185.9 / 192.2 / H9-N3-C2-S1 / 185.1 / 189.2 / H9-N3-C2-Se1 / 178.0 / 177.1
O10-H9-N3-C2 / -3.6 / 11.9 / O10-H9-N3-C2 / 2.8 / -5.0 / O10-H9-N3-C2 / -1.0 / 0.1
H11-O10-H9-N3 / 248.2 / 232.5 / H11-O10-H9-N3 / 238.6 / 248.9 / H11-O10-H9-N3 / 134.4 / 135.7
Table S18:Geometrical parameters of3-H2O-Cadducts at B3LYP/6-31+G* (L1) and MP2/6-31+G* (L2) theoretical levels. (Distances are in Å and angles in degrees)
Parameters / 3-H2O-CL1 / L2
C2-Se1 / 1.867 / 1.853
C3-C2 / 1.365 / 1.377
D4-C3 / 0.718 / 0.712
D5-C4 / 1.285 / 1.285
C6-D4 / 0.718 / 0.712
C7-C6 / 1.365 / 1.377
H8-C7 / 1.082 / 1.084
H9-C6 / 1.086 / 1.087
H10-C3 / 1.086 / 1.08
H11-C2 / 1.082 / 1.084
H12-Se1 / 2.627 / 2..652
O13-H12 / 0.972 / 0.973
H14-O13 / 0.969 / 0.91
C3-C2-Se1 / 111.57 / 111.49
D4-C3-C2 / 114.0 / 114.0
D5-D4-C3 / 90.0 / 90.0
C6-D4-D5 / 91.50 / 91.17
C7-C6-C3 / 114.74 / 114.59
H8-C7-C6 / 127.51 / 127.40
H9-C6-C3 / 122.70 / 123.20
H10-C3-C2 / 122.54 / 122.2
H11-C2-Se1 / 120.90 / 121.10
H12-Se1-C7 / 86.99 / 80.10
O3-H12-Se1 / 176.47 / 169.83
H14-O13-H12 / 104.89 / 104.29
D4-C3-C2-Se1 / 0.0 / 0.0
D5-D4-C3-C2 / 0.0 / 0.0
C6-D4-D5-C3 / 178.8 / 17.0
C7-C6-C3-Se1 / -0.4 / -0.3
H8-C7-C6-C3 / 180.1 / 180.2
H9-C6-C3-C2 / 180.2 / 180.2
H10-C3-C2-Se1 / 179.6 / 179.7
H11-C2-Se1-C7 / 180.3 / 180.5
H12-Se1-C7-C6 / 272.6 / 278.7
O13-H12-Se1-c2 / 323.6 / 316.9
H14-O13-H12-Se1 / -7.7 / -3.2
Table S19:Proton Affinities (in kcal/mol) of different sites of heterocyclic molecules.
Molecules / Site / B3LYP/6-311++G**//B3LYP/6-31+G* / MP2/6-311++G**//
MP2/6-31+G* / G2MP2
Furan
(1) / O1 / 166.75 / 163.63 / 166.16
C2 / 196.24 / 191.29 / 193.72
C3 / 184.39 / 179.98 / 183.23
Thiophene
(2) / S1 / 174.10 / 171.26 / 174.06
C2 / 197.94 / 193.49 / 193.93
C3 / 188.22 / 180.30 / 186.53
Selenophene
(3) / Se1 / 177.61 / 173.84 / 176.79
C2 / 201.00 / 187.97 / 197.05
C3 / 190.44 / 186.18 / 188.50
Isoxazole
(4) / O1 / 158.64 / 158.12 / 160.61
N2 / 203.25 / 201.51 / 200.53
C3 / 152.50 / 140.95 / 149.05
C4 / 173.67 / 168.71 / 173.82
C5 / 163.07 / 159.74 / 159.57
Isothiazole
(5) / S1 / 165.76 / 165.63 / 166.61
N2 / 213.74 / 213.83 / 208.89
C3 / 166.52 / 167.30 / 166.78
C4 / 178.05 / 176.59 / 177.55
C5 / 173.38 / 169.13 / 170.97
Isoselenazole (6) / Se1 / 148.48 / 141.04 / 170.75
N2 / 221.61 / 221.38 / 213.29
C3 / 169.13 / 168.58 / 168.46
C4 / 182.07 / 178.20 / 181.28
C5 / 177.66 / 171.5 / 174.83
Oxazole
(7) / O1 / - / - / 154.29
N3 / 207.63 / 203.70 / 207.93
C2 / 175.45 / 170.43 / 174.76
C4 / 174.75 / 175.52 / 173.44
C5 / 181.49 / 176.13 / 179.89
Thiazole
(8) / S1 / - / - / 162.66
N3 / 215.72 / 215.96 / 214.44
C2 / 181.21 / 177.93 / 179.43
C4 / 178.49 / 163.11 / 177.18
C5 / 185.62 / 180.76 / 182.71
Selenazole
(9) / Se1 / 134.08 / - / 167.47
N3 / 217.50 / 217.74 / 215.88
C2 / 185.03 / 178.13 / 183.25
C4 / 182.30 / 182.02 / 180.72
C5 / 189.21 / 183.16 / 186.37