1,3-dipolar cycloadditions. Part XX. DFT study of the configuration and conformation of C-aryl-N-phenyl nitrones and their reactivities as 1,3-dipoles to methyl and ethyl crotonates
IR@NISCAIR: CSIR-NISCAIR, New Delhi - ONLINE PERIODICALS REPOSITORY (NOPR)
View Archive Info| Field | Value | |
| Creator |
Acharjee, Nivedita
Banerji, Avijit |
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| Date |
2010-11-08T09:12:14Z
2010-11-08T09:12:14Z 2010-11 |
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| Identifier |
0975-0975(Online); 0376-4710(Print)
http://hdl.handle.net/123456789/10531 |
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| Description |
1444-1452
The preferred configurations and conformations of C-aryl-N-phenyl nitrones have been predicted theoretically by detailed comparison of DFT/B3LYP/6-311+G(2d,p) calculated gauge invariant atomic orbital nuclear magnetic shielding tensors and experimentally recorded chemical shift values. The frontier molecular orbital energies, electronic chemical potentials, chemical hardness, chemical softness and global electrophilicity indices of C-aryl-N-phenyl nitrones have been calculated at DFT/B3LYP/ 6-31+G(d,p) level of theory. Condensed Fukui functions and local electrophilicity indices have been computed to characterize the reactive sites and predict the preferred interactions of C-aryl-N-phenyl nitrones to methyl and ethyl crotonates. The softness matching indices have been evaluated to determine the regioselectivity of the cycloaddition reactions. The theoretical predictions were found to be in complete agreement with the experimental results implying that the DFT based reactivity indices correctly predict the regioselectivities of 1,3-dipolar cycloadditions of C-aryl-N-phenyl nitrones to methyl and ethyl crotonates. |
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| Language |
en_US
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| Publisher |
NISCAIR-CSIR, India
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| Rights |
<img src='http://nopr.niscair.res.in/image/cc-license-sml.png'> <a href='http://creativecommons.org/licenses/by-nc-nd/2.5/in' target='_blank'>CC Attribution-Noncommercial-No Derivative Works 2.5 India</a>
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| Source |
IJC-A Vol.49A(11) [November 2010]
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| Subject |
Theoretical chemistry
Density functional calculations Cycloadditions Dipolar cycloadditions Electrophilicity index Chemical shifts NMR shielding tensors Regioselectivity Nitrones Aryl phenyl nitrones |
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| Title |
1,3-dipolar cycloadditions. Part XX. DFT study of the configuration and conformation of C-aryl-N-phenyl nitrones and their reactivities as 1,3-dipoles to methyl and ethyl crotonates
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| Type |
Article
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