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Indian Journal of Chemistry -Section A (IJC-A) >
IJC-A Vol.49A [2010] >
IJC-A Vol.49A(11) [November 2010] >
| 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 |
| Authors: | Acharjee, Nivedita
Banerji, Avijit |
| Keywords: | Theoretical chemistry
Density functional calculations
Cycloadditions
Dipolar cycloadditions
Electrophilicity index
Chemical shifts
NMR shielding tensors
Regioselectivity
Nitrones
Aryl phenyl nitrones |
| Issue Date: | Nov-2010 |
| Publisher: | NISCAIR-CSIR, India |
| Abstract: | 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. |
| Page(s): | 1444-1452 |
| CC License: |  CC Attribution-Noncommercial-No Derivative Works 2.5 India |
| ISSN: | 0975-0975(Online); 0376-4710(Print) |
| Source: | IJC-A Vol.49A(11) [November 2010]
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