stability and aromaticity in the benzonitrile H 2 O complex with Na+ or Cl

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Electronic Supplementary Data A theoretical investigation on the cooperativity effect, reduced density gradient, stability and aromaticity in the benzonitrile H 2 O complex with Na+ or Cl Jiang-Bo Xie a, * & Wen-Jing Shi b a College of Materials Science and Engineering, North University of China, Taiyuan 030051, China Email: xjb209@126.com b The Third Hospital of Shanxi Medical University, Taiyuan 030053, China No. Contents Pg No. 1 Table S1 Interaction energy (E int. (kj/mol)) in binary system 2 2 Table S2 Interaction energy (E int., E int. or E int., kj/mol) and cooperativity energy (E coop., kj/mol) in Na + Benzonitrile(BN) H 2 O at the B3LYP/6-311++G(2d,p) level 2 3 Table S3 Interaction energy (E int., E int. or E int., kj/mol) and cooperativity energy (E coop., kj/mol) in Cl benzonitrile H 2 O ternary system at the B3LYP/6-311++G(2d,p) level 3 4 Table S4 APT (in bold), NBO (in plain) and Mulliken (in italic) charges (e), NBO charge transfers of H 2 O (Q CT (H 2 O), me) for the benzonitrile H 2 O systems at the B3LYP/6-311++G(2d,p) level 3 5 Table S5 APT (in bold), NBO (in plain) and Mulliken (in italic) charges (e), NBO charge transfers of H 2 O (Q CT (H 2 O), me) for the ternary systems with Cl at the B3LYP/6-311++G(2d,p) level 4 6 Table S6 APT (in bold), NBO (in plain) and Mulliken (in italic) charges (e), NBO charge transfers of H 2 O (Q CT (H 2 O), me) for the ternary systems with Na + at the B3LYP/6-311++G(2d,p) level 4 7 Table S7 APT (in bold), NBO (in plain) and Mulliken (in italic) charges (e), NBO charge transfers of H 2 O (Q CT (H 2 O), me) for the ternary systems with Ne(Na) at the B3LYP/6-311++G(2d,p) level 5 8 Table S8 APT (in bold), NBO (in plain) and Mulliken (in italic) charges (e), NBO charge transfers of H 2 O (Q CT (H 2 O), me) for the ternary systems with Ne(Cl) at the B3LYP/6-311++G(2d,p) level 5 9 Table S9 Isotropic (in plain) and anisotropic (in italic) NICS (0, π) and NICS (1) ( δ, ppm) involving the ring and C N bond in the binary and ternary complexes at the B3LYP/6-311++G(2d,p) level 6 10 Table S10 Bond dissociation energy (BDE (kj/mol)) of the C CN bond in the benzonitrile H 2 O (in italic) and Na + benzonitrile H 2 O (in plain) systems at the B3LYP/6-311++G** level 7 11 Table S11 Bond dissociation energy (BDE (kj/mol)) of the C CN bond in Cl benzonitrile H 2 O at the B3LYP/6-311++G(2d,p) level 7 12 Fig. S1 The optimized intermolecular distances and AIM results of binary-system conformations at B3LYP/6-311++G(2d,p) level 8 13 Fig. S2 The optimized structures of the Ne(Na) and Ne(Cl) ternary complexes at the B3LYP/6-311++G(2d,p) level 11 14 Fig. S3 R cʹ (anisotropic NICS, NICS(1) ternary /NICS(1) binary ) involving the C N bond vs. E coop in the ternary complexes with Na + at the B3LYP/6-311++G(2d,p) level 12 1

Table S1 Interaction energy (E int. (kj/mol)) in binary system Complex B3LYP/6-311++G(2d,p) MP2(full)/6-311++G(2d,p) I 19.7 ( 18.4) 20.3 ( 16.4) II 19.0 ( 17.4) 23.4 ( 18.5) III 9.3 ( 7.4) 11.7 ( 7.3) IV 9.1 ( 7.4) 12.8 ( 8.2) V 9.1 ( 7.3) 11.2 ( 7.0) Na + BN(A) 152.4 ( 150.4) 140.4 ( 134.4) Na + BN(B) 59.6 ( 56.4) 63.6 ( 53.9) Na + H 2 O 105.2 ( 102.3) 104.3 ( 97.9) Cl BN(A) 58.6 ( 56.8) 57.1 ( 56.8) Cl BN(A) 58.6 ( 57.0) 57.4 ( 57.0) Cl H 2 O 61.9 ( 60.5) 59.4 ( 59.2) Table S2 Interaction energy (E int., E int. or E int., kj/mol) and cooperativity energy (E coop., kj/mol) in Na + Benzonitrile(BN) H 2 O at the B3LYP/6-311++G(2d,p) level a Complex E int.(bn H2O) E int.(bn/h2o Na+) E int. E int.(na+ BN H2O) E coop. I-1(Na) 88.5( 87.3) b 174.1( 171.2) b 56.6 193.8( 189.3) 11.9 I-2(Na) 135.4( 133.4) c 6.4 240.6( 234.2) 12.0 88.2 ( 85.3) I-3(Na) 49.3 ( 46.0) c 0.3 154.5( 146.9) 11.5 94.9 ( 91.9) II-1(Na) 31.9( 30.2) 72.5 ( 69.2) 23.0 91.5 ( 85.9) 10.9 III-1(Na) 20.1( 18.3) 163.2( 161.2) 6.5 172.5( 168.4) 4.1 IV-1(Na) 20.5( 18.6) 163.8( 161.8) 6.5 172.9( 168.7) 4.7 IV-2(Na) 31.2( 29.3) 81.7 ( 78.5) 23.0 90.8 ( 85.4) 1.2 V-1(Na) 20.2( 18.4) 163.4( 161.4) 6.5 172.5( 168.4) 4.2 V-2(Na) 30.3( 28.5) 80.8 ( 77.6) 23.0 90.0 ( 84.4) 2.3 a The values in parenthesis are corrected for BSSE; those in bold mean E int.(h2o Na+). b E int.(bn H2O) = E BN H2O Na+ E BN E H2O Na+ ; E int.(h2o Na+) = E BN H2O Na+ E BN H2O E Na+. c E int.(bn Na+) = E BN Na+ H2O E BN E Na+ H2O. 2

Table S3 Interaction energy (E int., E int. or E int., kj/mol) and cooperativity energy (E coop., kj/mol) in Cl benzonitrile H 2 O ternary system at the B3LYP/6-311++G(2d,p) level a E int.(bn H2O) E int.(cl BN) E int.(cl H2O) E int.(bn H2O Cl ) E coop. I-1(Cl) b 25.8( 24.6) 64.7 ( 62.9) 84.4 ( 81.2) 1.2 I-2(Cl) b 29.8( 28.3) 68.7 ( 66.9) 88.4( 85.1) 6.2 II-1(Cl) 55.7( 54.0) c 95.3( 93.5) d 61.9( 60.5) 114.3( 109.9) 24.7 III-1(Cl) 50.5( 48.6) c 99.8( 98.0) d 61.8( 60.4) 109.1( 105.0) 19.7 III-2(Cl) 60.9( 59.0) c 110.2( 108.6) d 62.1( 60.8) 119.5( 115.2) 9.7 IV-1(Cl) b 118.0( 116.2) 55.0 ( 53.6) 113.6( 109.8) 3.0 V-1(Cl) 59.5( 57.7) c 109.0( 107.2) d 62.2( 60.8) 118.1( 113.8) 10.7 a The values in parenthesis are corrected for BSSE. b The value of E int.(h2o Cl) in I-1 and II-2 is 7.2 and 3.7 kj/mol, and that of E int.(h2o BN) in IV-1 is 4.4 kj/mol, respectively. c It means E int.(bn (H2O Cl )). d It means E int.(cl (BN H2O)). Table S4 APT (in bold), NBO (in plain) and Mulliken (in italic) charges (e), NBO charge transfers of H 2 O (Q CT (H 2 O), me) for the benzonitrile H 2 O systems at the B3LYP/6-311++G(2d,p) level complex O N H a Q CT (H 2 O) I 0.657, 0.945 0.621 II 0.594, 0.943 0.549 III 0.550, 0.929 0.589 IV 0.534, 0.930 0.578 V 0.551, 0.930 0.596 0.465, 0.369 0.235 0.459, 0.363 0.235 0.388, 0.323 0.223 0.391, 0.323 0.222 0.390, 0.323 0.220 0.439, 0.486, 0.383 8.33 0.112, 0.246, 0.242 0.51 0.109, 0.239, 0.266 4.01 0.067, 0.224, 0.179 2.73 0.070, 0.223, 0.178 0.113, 0.236, 0.263 3.88 3

Table S5 APT (in bold), NBO (in plain) and Mulliken (in italic) charges (e), NBO charge transfers of H 2 O (Q CT (H 2 O), me) for the ternary systems with Cl at the B3LYP/6-311++G(2d,p) level complex Cl O N H a H b Q CT I-1(Cl) 0.991, 0.965 0.908 I-2(Cl) 1.002, 0.970 0.917 II-1(Cl) 0.970, 0.918 0.853 III-1(Cl) 0.946, 0.919 0.862 III-2(Cl) 0.978, 0.919 0.854 IV-1(Cl) 0.987, 0.940 0.819 V-1(Cl) 0.968, 0.919 0.857 0.694, 0.961 0.645 0.697, 0.959 0.642 0.740, 0.994 0.574 0.766, 0.996 0.590 0.762, 0.995 0.579 0.758, 0.985 0.620 0.773, 0.996 0.588 a The values of hydrogen atoms in benzonitrile. b The values of hydrogen atoms in H 2 O. 0.578, 0.415 0.287 0.631, 0.425 0.300 0.474, 0.359 0.263 0.457, 0.363 0.259 0.508, 0.366 0.271 0.500, 0.361 0.268 0.497, 0.363 0.269 0.234,0.287 0.126 0.139,0.259, 0.136 0.200,0.275,0.123 0.139,0.250,0.248 0.223,0.279,0.122 0.180,0.210,0.190 0.154,0.277, 0.134 0.142,0.250,0.227 0.224, 0.275,0.142 0.130,0.255,0.133 0.171,0.263,0.122 0.209,0.277,0.153 0.155,0.250, 0.224 0.480, 0.496 0.410 0.488, 0.496 0.411 0.463, 0.497 0.272 0.478, 0.497 0.283 0.473, 0.497 0.280 0.501, 0.500 0.313 0.478, 0.497 0.284 14.03 13.99 50.75 52.91 51.40 41.86 52.67 Table S6 APT (in bold), NBO (in plain) and Mulliken (in italic) charges (e), NBO charge transfers of H 2 O (Q CT (H 2 O), me) for the ternary systems with Na + at the B3LYP/6-311++G(2d,p) level complex Na + O N H a Q CT (H 2 O) I-1(Na) 0.965, 0.989 0.895 I-2(Na) 0.983, 0.956 0.661 I-3(Na) 0.776, 0.934 0.809 II-1(Na) 0.777, 0.966 0.843 III-1(Na) 1.008, 0.981 0.831 IV-1(Na) 1.009, 0.981 0.828 IV-2(Na) 0.777, 0.966 0.842 V-1(Na) 1.009, 0.981 0.818 V-2(Na) 0.777, 0.966 0.833 0.892, 1.062 0.715 0.625, 0.990 0.540 0.596, 0.985 0.529 0.559, 0.951 0.590 0.567, 0.939 0.603 0.552, 0.941 0.582 0.567, 0.950 0.587 0.575, 0.940 0.603 0.590, 0.948 0.607 0.728, 0.474 0.317 0.766, 0.542 0.061 0.217, 0.229 0.127 0.211, 0.227 0.124 0.829, 0.589 0.232 0.837, 0.590 0.234 0.210, 0.225 0.125 0.837, 0.589 0.238 0.210, 0.224 0.124 a The values of hydrogen atom in H 2 O for I and I-1, or in benzonitrile for the other complexes 0.686, 0.520, 0.485 45.35 13.98 24.66 0.137, 0.267, 0.285 5.82 0.110, 0.256, 0.257 0.153, 0.257, 0.294 6.43 0.098, 0.242, 0.209, 4.08 0.103, 0.239, 0.224 0.119, 0.259, 0.253 5.39 0.120, 0.256, 0.246 0.162, 0.255, 0.305 6.51 0.191,0.273, 0.342 8.90 4

Table S7 APT (in bold), NBO (in plain) and Mulliken (in italic) charges (e), NBO charge transfers of H 2 O (Q CT (H 2 O), me) for the ternary systems with Ne(Na) at the B3LYP/6-311++G(2d,p) level complex Ne O N H a Q CT (H 2 O) I-1(Ne(Na)) 0.000, 0.000 0.006 I-2(Ne(Na)) 0.002, 0.000 0.019 I-3(Ne(Na)) 0.000, 0.000 0.019 II-1(Ne(Na)) 0.000, 0.000 0.018 III-1(Ne(Na)) 0.000, 0.000 0.006 IV-1(Ne(Na)) 0.000, 0.000 0.006 IV-2(Ne(Na)) 0.000, 0.000 0.017 V-1(Ne(Na)) 0.000, 0.000 0.006 V-2(Ne(Na)) 0.000, 0.000 0.017 0.656, 0.945 0.618 0.657, 0.945 0.620 0.594, 0.943 0.548 0.657, 0.945 0.620 0.550, 0.929 0.588 0.533, 0.930 0.575 0.533, 0.930 0.575 0.551, 0.930 0.596 0.551, 0.930 0.596 0.466, 0.369 0.229 0.465, 0.369 0.231 0.458, 0.364 0.235 0.465, 0.369 0.242 0.386, 0.323 0.234 0.389, 0.323 0.233 0.391, 0.323 0.223 0.389, 0.323 0.229 0.390, 0.323 0.222 a The values of hydrogen atom in H 2 O for I and I-1, or in benzonitrile for the other complexes 0.438, 0.486, 0.371 8.38 8.36 0.50 0.064, 0.220, 0.169 8.34 0.044, 0.214, 0.143 0.109, 0.239, 0.267 4.05 0.068, 0.222, 0.182, 2.73 0.069, 0.226, 0.185 0.066, 0.223, 0.180 2.71 0.072, 0.224, 0.191 0.112, 0.236, 0.264 3.87 0.112,0.236, 0.269 3.88 Table S8 APT (in bold), NBO (in plain) and Mulliken (in italic) charges (e), NBO charge transfers of H 2 O (Q CT (H 2 O), me) for the ternary systems with Ne(Cl) at the B3LYP/6-311++G(2d,p) level complex Ne O N H a H b Q CT I-1(Ne(Cl)) 0.001, 0.000 0.018 I-2(Ne(Cl)) 0.001, 0.000 0.019 II-1(Ne(Cl)) 0.001, 0.000 0.018 III-1(Ne(Cl)) 0.003, 0.000 0.013 III-2(Ne(Cl)) 0.001, 0.000 0.017 IV-1(Ne(Cl)) 0.004, 0.000 0.013 V-1(Ne(Cl)) 0.004, 0.000 0.013 a The values of hydrogen atoms in benzonitrile b The values of hydrogen atoms in H 2 O. 0.659, 0.945 0.621 0.658, 0.945 0.621 0.594, 0.943 0.551 0.553, 0.930 0.560 0.550, 0.929 0.587 0.536, 0.930 0.583 0.555, 0.931 0.604 0.463, 0.369 0.226 0.466, 0.369 0.234 0.459, 0.364 0.236 0.388, 0.323 0.222 0.388, 0.323 0.223 0.391, 0.323 0.222 0.391, 0.323 0.220 0.046,0.214 0.131 0.045,0.214, 0.139 0.048,0.211,0.134 0.111,0.245,0.233 0.042,0.212,0.141 0.058,0.216,0.152 0.111,0.239, 0.261 0.110,0.239,0.261 0.042, 0.208,0.135 0.037,0.209,0.146 0.067,0.221,0.172 0.040,0.210,0.133 0.113,0.236, 0.262 0.438, 0.486 0.380 0.439, 0.486 0.383 0.266, 0.462 0.279 0.274, 0.467 0.281 0.268, 0.467 0.288 0.273, 0.467 0.281 0.275, 0.467 0.283 8.47 8.33 0.72 3.72 4.01 2.51 3.52 5

Table S9 Isotropic (in plain) and anisotropic (in italic) NICS (0, π) and NICS (1) ( δ, ppm) involving the ring and C N bond in the binary and ternary complexes at the B3LYP/6-311++G(2d,p) level complex NICS(0,π) (ring) NICS(1) (ring) NICS(0,π) (C N bond) NICS(1) (C N bond) I 8.044, 8.104 10.002, 27.122 70.943, 31.433 10.456, 7.042 II 8.033, 7.788 9.922, 27.038 70.469, 27.932 10.333, 6.078 III 7.914, 7.945 9.874, 27.087 70.678, 29.622 10.518, 6.900 IV 7.879, 7.983 9.902, 27.046 70.695, 29.822 10.493, 6.965 V 7.960, 7.953 9.957, 27.000 70.702, 29.900 10.486, 6.954 Na + BN(A) 7.929, 7.198 9.956, 26.462 71.547, 31.342 9.627, 7.941 Na + BN(B) 7.110, 10.115 9.474, 28.662 69.131, 26.972 10.456, 7.512 I-1(Na) 7.977, 7.540 10.095, 26.724 71.310, 32.533 10.103, 7.526 I-2(Na) 7.961, 7.293 9.980, 26.521 71.592, 31.970 9.719, 7.600 I-3(Na) 7.382, 10.376 9.638, 28.717 69.349, 27.520 10.439, 7.774 II-1(Na) 7.025, 9.951 9.483, 28.421 69.316, 27.301 10.464, 7.371 III-1(Na) 7.819, 6.791 9.575, 26.249 71.515, 31.308 9.567, 7.869 IV-1(Na) 7.733, 6.783 9.820, 26.220 71.456, 31.322 9.591, 7.916 IV-2(Na) 6.995, 9.848 9.626, 28.473 69.115, 27.515 10.451, 7.492 V-1(Na) 7.837, 6.685 9.935, 26.080 71.512, 31.310 9.558, 7.891 V-2(Na) 7.012, 9.755 9.392, 28.369 69.116, 27.545 10.880, 6.729 Cl BN(A) 7.776, 7.089 9.851, 26.446 71.169, 30.595 10.378, 6.890 Cl BN(B) 7.771, 7.086 9.903, 26.407 71.072, 30.621 10.346, 6.859 I-1(Cl) 7.781, 6.910 9.923, 26.190 71.244, 32.028 10.226, 6.491 I-2(Cl) 7.746, 6.769 9.906, 26.112 71.270, 32.276 10.134, 6.732 II-1(Cl) 7.829, 7.281 9.968, 26.485 71.059, 30.305 10.467, 7.012 III-1(Cl) 7.808, 7.293 10.055, 26.514 71.010, 30.172 10.548, 7.114 III-2(Cl) 7.752, 7.024 9.945, 26.422 71.063, 30.759 10.506, 7.422 V-1(Cl) 7.852, 7.171 9.950, 26.467 71.133, 30.568 10.440, 6.885 6

Table S10 Bond dissociation energy (BDE (kj/mol)) of the C CN bond in the benzonitrile H 2 O (in italic) and Na + benzonitrile H 2 O (in plain) systems at the B3LYP/6-311++G** level I-1(Na) I-2(Na) I-3(Na) II-1(Na) III-1(Na) IV-1(Na) IV-2(Na) V-1(Na) V-2(Na) 633.1 649.6 546.9 545.6 673.3 674.0 545.6 673.8 545.4 589.6 590.8 580.9 581.2 580.9 Table S11 Bond dissociation energy (BDE (kj/mol)) of the C CN bond in Cl benzonitrile H 2 O at the B3LYP/6-311++G(2d,p) level I-1(Cl) I-2(Cl) II-1(Cl) III-1(Cl) III-2(Cl) IV-1(Cl) V-1(Cl) 621.2 626.3 597.8 595.1 603.4 601.3 601.0 7

(I) (II) (III) (IV) (V) 8

Na + BN(A) Na + BN (B) Na + H 2 O Cl BN(A) 9

Cl BN(B) Cl H 2 O Fig. S1 The optimized intermolecular distances and AIM results of binary-system conformations at B3LYP/6-311++G(2d,p) level. 10

I-1(Ne(Na)) I-2(Ne(Na)) I-3(Ne(Na)) II-1(Ne(Na)) III-1(Ne(Na)) IV-1(Ne(Na)) IV-2(Ne(Na)) V-1(Ne(Na)) V-2(Ne(Na)) I-1(Ne(Cl)) I-2(Ne(Cl)) II-1(Ne(Cl)) III-1(Ne(Cl)) III-2(Ne(Cl)) IV-1(Ne(Cl)) V-1(Ne(Cl)) : C; : H; : O; : N; : Ne Fig. S2 The optimized structures of the Ne(Na) and Ne(Cl) ternary complexes at the B3LYP/6-311++G(2d,p) level (Ne(Na) and Ne(Cl) mean the ternary complexes with Ne in place of Na + and Cl ). 11

Fig. S3 R cʹ (anisotropic NICS, NICS(1) ternary /NICS(1) binary ) involving the C N bond vs. E coop in the ternary complexes with Na + at the B3LYP/6-311++G(2d,p) level. 12

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