C∙∙∙O and Si∙∙∙O Tetrel Bonds: Substituent Effects and Transfer of the SiF3 Group
Abstract
:1. Introduction
2. Theoretical Methods
3. Results
4. Discussion
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Vmin | RO | RN | ΔRN | RO/RN | γO a | γN a | α | |
---|---|---|---|---|---|---|---|---|
S-CF3∙∙∙PO-NO2 | −27.6 | 3.123 | 1.431 | 0.005 | 2.183 | 0.970 | 0.441 | 110.2 |
S-CF3∙∙∙PO | −40.8 | 3.151 | 1.436 | 0.010 | 2.193 | 0.979 | 0.442 | 109.9 |
S-CF3∙∙∙PO-CH3 | −43.3 | 3.119 | 1.437 | 0.011 | 2.169 | 0.969 | 0.442 | 109.8 |
S-CF3∙∙∙PO-OH | −43.9 | 3.115 | 1.437 | 0.011 | 2.169 | 0.967 | 0.442 | 109.8 |
S-CF3∙∙∙PO-OCH3 | −45.2 | 3.144 | 1.437 | 0.011 | 2.188 | 0.976 | 0.442 | 109.8 |
S-CF3∙∙∙PO-NH2 | −47.7 | 3.085 | 1.438 | 0.012 | 2.146 | 0.958 | 0.442 | 109.7 |
S-CF3∙∙∙PO-Li | −55.2 | 3.097 | 1.440 | 0.014 | 2.151 | 0.962 | 0.443 | 109.6 |
S-SiF3∙∙∙PO-NO2 | −27.6 | 1.902 | 1.819 | 0.080 | 1.045 | 0.526 | 0.499 | 94.3 |
S-SiF3∙∙∙PO-CN | −29.5 | 1.896 | 1.821 | 0.082 | 1.042 | 0.524 | 0.499 | 94.2 |
S-SiF3∙∙∙PO-F | −39.5 | 1.874 | 1.829 | 0.090 | 1.025 | 0.518 | 0.501 | 93.5 |
S-SiF3∙∙∙PO | −40.8 | 1.874 | 1.831 | 0.092 | 1.024 | 0.518 | 0.502 | 93.3 |
S-SiF3∙∙∙PO-CH3 | −43.3 | 1.866 | 1.834 | 0.095 | 1.017 | 0.515 | 0.502 | 93.1 |
S-SiF3∙∙∙PO-OH | −43.9 | 1.860 | 1.834 | 0.095 | 1.014 | 0.514 | 0.502 | 93.0 |
S-SiF3∙∙∙PO-OCH3 | −45.2 | 1.856 | 1.836 | 0.097 | 1.011 | 0.513 | 0.503 | 92.9 |
S-SiF3∙∙∙PO-NH2 | −47.7 | 1.848 | 1.841 | 0.102 | 1.004 | 0.510 | 0.504 | 91.2 |
S-SiF3∙∙∙PO-Li | −55.2 | 1.842 | 1.849 | 0.110 | 0.996 | 0.509 | 0.507 | 92.2 |
Eint | Eb | DE | |
---|---|---|---|
S-CF3∙∙∙PO-NO2 | −2.69 | −2.55 | 0.14 |
S-CF3∙∙∙PO | −2.33 | −2.12 | 0.21 |
S-CF3∙∙∙PO-CH3 | −2.36 | −2.13 | 0.23 |
S-CF3∙∙∙PO-OH | −2.63 | −2.35 | 0.28 |
S-CF3∙∙∙PO-OCH3 | −2.62 | −2.36 | 0.26 |
S-CF3∙∙∙PO-NH2 | −2.37 | −2.11 | 0.26 |
S-CF3∙∙∙PO-Li | −2.01 | −1.62 | 0.39 |
S-SiF3∙∙∙PO-NO2 | −46.59 | −15.12 | 31.47 |
S-SiF3∙∙∙PO-CN | −48.12 | −16.29 | 31.83 |
S-SiF3∙∙∙PO-F | −56.59 | −22.39 | 34.20 |
S-SiF3∙∙∙PO | −56.45 | −21.82 | 34.63 |
S-SiF3∙∙∙PO-CH3 | −59.29 | −23.78 | 35.51 |
S-SiF3∙∙∙PO-OH | −61.52 | −25.64 | 35.88 |
S-SiF3∙∙∙PO-OCH3 | −62.65 | −26.29 | 36.36 |
S-SiF3∙∙∙PO-NH2 | −66.58 | −28.50 | 38.08 |
S-SiF3∙∙∙PO-Li | −69.15 | −29.76 | 39.39 |
T∙∙∙O a | N-T | |||||
---|---|---|---|---|---|---|
ρ | ∇2ρ | H | ρ | ∇2ρ | H | |
S-CF3∙∙∙PO-NO2 | 0.0067 | 0.0372 | 0.0018 | 0.2926 | −0.8536 | −0.3242 |
S-CF3∙∙∙PO | 0.0072 | 0.0390 | 0.0016 | 0.2894 | −0.8362 | −0.3191 |
S-CF3∙∙∙PO-CH3 | 0.0074 | 0.0403 | 0.0016 | 0.2885 | −0.8316 | −0.3177 |
S-CF3∙∙∙PO-OH | 0.0066 | 0.0361 | 0.0018 | 0.2885 | −0.8312 | −0.3176 |
S-CF3∙∙∙PO-OCH3 | 0.0066 | 0.0357 | 0.0017 | 0.2882 | −0.8294 | −0.3169 |
S-CF3∙∙∙PO-NH2 | 0.0078 | 0.0423 | 0.0017 | 0.2876 | −0.8271 | −0.3166 |
S-CF3∙∙∙PO-Li | 0.0071 | 0.0388 | 0.0018 | 0.2853 | −0.8170 | −0.3142 |
S-SiF3∙∙∙PO-NO2 | 0.0707 | 0.3233 | −0.0162 | 0.1004 | 0.4831 | −0.0279 |
S-SiF3∙∙∙PO-CN | 0.0716 | 0.3317 | −0.0162 | 0.1000 | 0.4796 | −0.0278 |
S-SiF3∙∙∙PO-F | 0.0758 | 0.3686 | −0.0163 | 0.0982 | 0.4656 | −0.0272 |
S-SiF3∙∙∙PO | 0.0756 | 0.3680 | −0.0161 | 0.0976 | 0.4612 | −0.0269 |
S-SiF3∙∙∙PO-OH | 0.0783 | 0.3917 | −0.0163 | 0.0969 | 0.4551 | −0.0267 |
S-SiF3∙∙∙PO-NH2 | 0.0808 | 0.4139 | −0.0164 | 0.0955 | 0.4444 | −0.0263 |
S-SiF3∙∙∙PO-OCH3 | 0.0790 | 0.3990 | −0.0162 | 0.0965 | 0.4524 | −0.0266 |
S-SiF3∙∙∙PO-NH2 | 0.0808 | 0.4139 | −0.0164 | 0.0955 | 0.4444 | −0.0263 |
S-SiF3∙∙∙PO-Li | 0.0815 | 0.4247 | −0.0161 | 0.0937 | 0.4308 | −0.0257 |
CT a | E | |
---|---|---|
S-CF3∙∙∙PO-NO2 | 0.0013 | −0.31 |
S-CF3∙∙∙PO | 0.0009 | −0.36 |
S-CF3∙∙∙PO-CH3 | 0.0004 | −0.39 |
S-CF3∙∙∙PO-OH | 0.0001 | −0.39 |
S-CF3∙∙∙PO-OCH3 | 0.0006 | −0.39 |
S-CF3∙∙∙PO-NH2 | 0.0005 | −0.44 |
S-CF3∙∙∙PO-Li | 0.0002 | −0.43 |
S-SiF3∙∙∙PO-NO2 | 0.1755 | −54.50 |
S-SiF3∙∙∙PO-CN | 0.1780 | −55.26 |
S-SiF3∙∙∙PO-F | 0.1900 | −58.50 |
S-SiF3∙∙∙PO | 0.1907 | −58.67 |
S-SiF3∙∙∙PO-CH3 | 0.1942 | −60.00 |
S-SiF3∙∙∙PO-OH | 0.1961 | −60.58 |
S-SiF3∙∙∙PO-OCH3 | 0.1977 | −61.20 |
S-SiF3∙∙∙PO-NH2 | 0.2024 | −62.59 |
S-SiF3∙∙∙PO-Li | 0.2059 | −64.08 |
Ees | Eex | Erep | Epol | Edisp | ΔEtotal | |
---|---|---|---|---|---|---|
S-CF3∙∙∙PO-NO2 | −3.61 | −2.77 | 12.79 | −0.74 | −8.45 | −2.78 |
S-CF3∙∙∙PO | −3.37 | −3.12 | 13.68 | −0.88 | −8.69 | −2.38 |
S-CF3∙∙∙PO-CH3 | −3.50 | −3.30 | 14.17 | −1.03 | −8.76 | −2.42 |
S-CF3∙∙∙PO-OH | −3.70 | −3.23 | 13.92 | −1.04 | −8.68 | −2.73 |
S-CF3∙∙∙PO-OCH3 | −3.64 | −3.26 | 14.11 | −1.05 | −8.86 | −2.70 |
S-CF3∙∙∙PO-NH2 | −3.80 | −3.69 | 15.17 | −1.14 | −8.95 | −2.42 |
S-CF3∙∙∙PO-Li | −2.97 | −3.28 | 13.73 | −1.24 | −8.31 | −2.06 |
S-SiF3∙∙∙PO-NO2 | −74.86 | −54.07 | 169.62 | −63.03 | −26.97 | −49.31 |
S-SiF3∙∙∙PO-CN | −76.91 | −54.94 | 172.17 | −64.04 | −27.17 | −50.89 |
S-SiF3∙∙∙PO-F | −88.66 | −59.35 | 185.02 | −68.96 | −27.67 | −59.62 |
S-SiF3∙∙∙PO | −87.17 | −58.59 | 182.73 | −68.78 | −27.68 | −59.51 |
S-SiF3∙∙∙PO-CH3 | −90.66 | −59.97 | 186.83 | −70.93 | −27.75 | −62.48 |
S-SiF3∙∙∙PO-OH | −94.57 | −61.55 | 191.51 | −72.18 | −27.92 | −64.72 |
S-SiF3∙∙∙PO-OCH3 | −95.80 | −62.06 | 193.06 | −73.16 | −27.90 | −65.85 |
S-SiF3∙∙∙PO-NH2 | −100.42 | −63.69 | 197.82 | −75.37 | −28.25 | −69.91 |
S-SiF3∙∙∙PO-Li | −100.95 | −63.45 | 196.96 | −77.16 | −28.09 | −72.69 |
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Niu, Z.; Wu, Q.; Li, Q.; Scheiner, S. C∙∙∙O and Si∙∙∙O Tetrel Bonds: Substituent Effects and Transfer of the SiF3 Group. Int. J. Mol. Sci. 2023, 24, 11884. https://doi.org/10.3390/ijms241511884
Niu Z, Wu Q, Li Q, Scheiner S. C∙∙∙O and Si∙∙∙O Tetrel Bonds: Substituent Effects and Transfer of the SiF3 Group. International Journal of Molecular Sciences. 2023; 24(15):11884. https://doi.org/10.3390/ijms241511884
Chicago/Turabian StyleNiu, Zhihao, Qiaozhuo Wu, Qingzhong Li, and Steve Scheiner. 2023. "C∙∙∙O and Si∙∙∙O Tetrel Bonds: Substituent Effects and Transfer of the SiF3 Group" International Journal of Molecular Sciences 24, no. 15: 11884. https://doi.org/10.3390/ijms241511884