| Title |
Microsolvation effects on the reactivity of oxy-nucleophiles: the case of gas-phase SN2 reactions of YO−(CH3OH)n=1,2 towards CH3Cl
|
|---|---|
| Published in |
Journal of Molecular Modeling, May 2017
|
| DOI | 10.1007/s00894-017-3351-7 |
| Pubmed ID | |
| Authors |
Liu Yun-Yun, Qiu Fang-Zhou, Zhu Jun, Ren Yi, Lau Kai-Chung |
| Abstract |
The modified G4(MP2) method was applied to explore microsolvation effects on the reactivity of four solvated normal oxy-nucleophiles YO(-)(CH3OH) n=1,2 (Y = CH3, C2H5, FC2H4, ClC2H4), and five α-oxy-nucleophiles YO(-)(CH3OH) n=1,2 (Y = HO, CH3O, F, Cl, Br), in gas-phase SN2 reactions towards the substrate CH3Cl. Based on a Brønsted-type plot, our calculations reveal that the overall activation barriers of five microsolvated α-oxy-nucleophiles are obviously smaller than the prediction from the correlation line constructed by four normal microsolvated ones to different degrees, and clearly demonstrate the existence of an α-effect in the presence of one or two methanol molecule(s). Moreover, it was found that the α-effect of the mono-methanol microsolvated α-nucleophile is stronger than that of the monohydrated α-nucleophile. However, the α-effect of YO(-)(CH3OH)2 becomes weaker for Y = HO and CH3O, whereas it becomes stronger for Y = F, Cl, Br than that of YO(-)(H2O)2, which can be explained by analyses of the activation strain model in the two cases. It was also found that the rationale about the low ionization energy of α-nucleophile inducing the α-effect was not widely significant. Graphical abstract Variation of alpha-effect in the gas-phase SN2 reaction with the microsolvation. |
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Geographical breakdown
| Country | Count | As % |
|---|---|---|
| Unknown | 1 | 100% |
Demographic breakdown
| Type | Count | As % |
|---|---|---|
| Members of the public | 1 | 100% |
Mendeley readers
The data shown below were compiled from readership statistics for 7 Mendeley readers of this research output. Click here to see the associated Mendeley record.
Geographical breakdown
| Country | Count | As % |
|---|---|---|
| Unknown | 7 | 100% |
Demographic breakdown
| Readers by professional status | Count | As % |
|---|---|---|
| Student > Bachelor | 2 | 29% |
| Unspecified | 1 | 14% |
| Professor | 1 | 14% |
| Student > Ph. D. Student | 1 | 14% |
| Professor > Associate Professor | 1 | 14% |
| Other | 1 | 14% |
| Readers by discipline | Count | As % |
|---|---|---|
| Chemistry | 5 | 71% |
| Pharmacology, Toxicology and Pharmaceutical Science | 1 | 14% |
| Unspecified | 1 | 14% |
Attention Score in Context
This research output has an Altmetric Attention Score of 1. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 22 May 2017.
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#20,421,487
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#636
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Outputs of similar age from Journal of Molecular Modeling
#14
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