Modes of Neighbouring Group Participation by the Methyl Selenyl Substituent in β-Methylselenylmethyl-substituted 1-Phenylethyl Carbenium Ions
Abstract
:1. Introduction
2. Methods
3. Results and Discussion
10 | 11 | 12 | 13 | |
---|---|---|---|---|
Se-CH2 (Å) | 2.012 | 2.011 | 2.010 | 2.010 |
Se-CH2-C+ (°) | 98.84 | 93.41 | 84.78 | 78.96 |
Se…C(+) Å | 2.664 | 2.554 | 2.372 | 2.245 |
C(Ar)-C+ | 1.389 | 1.403 | 1.423 | 1.452 |
pKR+ a | −12.4 [ 22] | <−20 [ 23] | ||
Vertical interaction E(2) (kJ mol−1) | 55.7 | 73.3 | 211.6 | - |
σC-Seenergy (a.u.) | −0.641 | −0.653 | −0.660 | |
σC-Sepopulation | 1.891 | 1.866 | 1.820 | |
Overlap, F(i,j) (a.u.) | 0.076 | 0.087 | 0.139 | |
Nonvertical interaction E(2) (kJ mol−1) | 17.2 | 49.0 | 418.4 | - |
nSeenergy (a.u.) | −0.363 | −0.379 | −0.397 | |
nSepopulation | 1.799 | 1.727 | 1.606 | |
F(i,j) (a.u.) | 0.037 | 0.046 | 0.083 |
4. Conclusions
Supplementary Materials
Acknowledgments
Conflicts of Interest
References
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Harris, B.L.; White, J.M. Modes of Neighbouring Group Participation by the Methyl Selenyl Substituent in β-Methylselenylmethyl-substituted 1-Phenylethyl Carbenium Ions. Molecules 2013, 18, 11705-11711. https://doi.org/10.3390/molecules181011705
Harris BL, White JM. Modes of Neighbouring Group Participation by the Methyl Selenyl Substituent in β-Methylselenylmethyl-substituted 1-Phenylethyl Carbenium Ions. Molecules. 2013; 18(10):11705-11711. https://doi.org/10.3390/molecules181011705
Chicago/Turabian StyleHarris, Benjamin L., and Jonathan M. White. 2013. "Modes of Neighbouring Group Participation by the Methyl Selenyl Substituent in β-Methylselenylmethyl-substituted 1-Phenylethyl Carbenium Ions" Molecules 18, no. 10: 11705-11711. https://doi.org/10.3390/molecules181011705